1,5-diphenylpyrazolyl-3-oxyalkyl acids and 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and the use thereof for control of unwanted plant growth

ABSTRACT

The present invention relates to novel herbicidally active, substituted 1,5-diphenylpyrazolyl-3-oxyalkyl acids and 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and derivatives thereof according to the general formula (I) or agrochemically acceptable salts thereof, to processes for preparation thereof and to the use thereof for control of broadleaved weeds and weed grasses in crops of useful plants and for general control of broadleaved weeds and weed grasses in areas of the environment where plant growth is troublesome. The derivatives of the 1,5-diphenylpyrazolyl-3-oxyalkyl acids and 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids especially include the esters, salts and amides thereof.

The present invention relates to novel herbicidally active, substituted1,5-diphenylpyrazolyl-3-oxyalkyl acids and1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and derivatives thereofaccording to the general formula (I) or agrochemically acceptable saltsthereof, to processes for preparation thereof and to the use thereof forcontrol of broadleaved weeds and weed grasses in crops of useful plantsand for general control of broadleaved weeds and weed grasses in areasof the environment where plant growth is troublesome.

The derivatives of the 1,5-diphenylpyrazolyl-3-oxyalkyl acids and1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids especially include theesters, salts and amides thereof.

The prior art discloses biological effects of substituted1,5-diphenylpyrazolyl-3-oxyacetic acids and substituted1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and processes for preparingthese compounds. DE 2828529 A1 describes the preparation and thelipid-lowering effect of 1,5-diphenylpyrazolyl-3-oxyacetic acids. CN101284815 discloses 1,5-diphenylpyrazolyl-3-oxyacetic acid derivativesas bactericidally active agrochemicals. Journal of HeterocyclicChemistry (2012), 49(6), 1370-1375 describes further syntheses and thefungicidal action of 1,5-diphenylpyrazolyl-3-oxyacetic acids. Thesynthesis of substituted 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acidsand the pharmaceutical action thereof as FXR and LXR modulators aredescribed in WO 2008/073825 A1.

Substituted 1,5-diphenylpyrazolyl-3-oxyalkyl acids and substituted1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids are unknown as herbicidesto date.

It is a feature of all 1,5-diphenylpyrazolyl-3-oxyalkyl acid derivativesand all 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acid derivatives from theabovementioned sources that they are unsubstituted in the 4 position ofthe pyrazole.

By contrast, a common feature of the 1,5-diphenylpyrazolyl-3-oxyalkylacids and 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids according to theinvention is a further substituent in the 4 position of the pyrazolering. The present invention thus provides1,5-diphenylpyrazolyl-3-oxyalkyl acids and1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids substituted exclusively inthe 4 position of the pyrazole (R³ hydrogen), and derivatives thereof.

WO 2008/083233 A2 describes such 1,5-diphenylpyrazolyl-3-oxyalkyl acidssubstituted in 4 position of the pyrazole and derivatives thereof assubstances suitable for breaking up cell aggregates. Ethyl[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate is specificallydisclosed.

In addition, the synthesis of some4-chloro-1,5-diphenylpyrazolyl-3-oxyacetic acids and ethyl estersthereof is described in European Journal of Organic Chemistry (2011),2011 (27), 5323-5330, specifically:

-   [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid-   {[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic    acid-   {[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic    acid-   ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate-   ethyl    {[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate-   ethyl    {[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate.

WO 2008/141154 discloses:2-(4-chloro-1,5-diphenylpyrazol-3-yl)oxypropanoic acid and2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.

There is no description of the herbicidal action of these compounds.

The 1-phenyl-5-thienylpyrazolyl-3-oxyacetic acids or1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and derivatives thereofthat are encompassed by this application are unknown to date.

It is an object of the present invention to provide novel pyrazolederivatives, namely of 1,5-diphenylpyrazolyl-3-oxyalkyl acids and1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and derivatives thereof,which can be used as herbicides or plant growth regulators, havingsatisfactory herbicidal action and a broad spectrum of activity againstharmful plants and/or having high selectivity in crops of useful plants.

The object is achieved by substituted pyrazolyl-3-oxoalkyl acidsfeaturing a variable substituent in the 4 position of the pyrazole ring,i.e. by 4-substituted 1,5-diphenylpyrazolyl-3-oxyalkyl acid derivativesand 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acid derivatives, having verygood herbicidal action and also very good selectivity.

Surprisingly, these compounds are highly effective against a broad rangeof economically important weed grasses and broadleaved weeds. At thesame time, the compounds exhibit good crop plant compatibility.Therefore, given good efficacy against harmful plants, they can be usedselectively in crop plants.

The present invention therefore provides substituted1,5-diphenylpyrazolyl-3-oxyalkyl acids and1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids of the general formula (I)

and the agrochemically acceptable salts thereof, where

A is selected from the group consisting of A1-A3,

R¹ is selected from the group consisting of

-   -   OR^(1a) and    -   NR⁹R¹⁰; where        -   R^(1a) is selected from the group consisting of            -   hydrogen;            -   methyl, ethyl which is unsubstituted or substituted by                one or more substituents selected from the group                consisting of halogen, (C₃-C₆)-cycloalkyl,                (C₁-C₄)-trialkylsilyl, (C₁-C₆)-alkoxy, cyano and nitro;            -   (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl;            -   (C₂-C₆)-alkynyl,            -   (C₃-C₆)-cycloalkyl which is unsubstituted or substituted                by one or more substituents selected from the group                consisting of halogen, (C₁-C₆)-alkyl,                (C₃-C₆)-cycloalkyl;            -   (C₁-C₄)-alkyl-SO—(C₁-C₄)-alkyl,                (C₁-C₄)-alkyl-SO₂—(C₁-C₄)-alkyl;            -   heterocyclyl, heteroaryl and aryl which is unsubstituted                or substituted by one or more substituents selected from                the group consisting of halogen, (C₁-C₆)-alkyl,                (C₁-C₆)-haloalkyl;            -   heterocyclyl-(C₁-C₄)-alkyl, heteroaryl-(C₁-C₄)-alkyl and                aryl-(C₁-C₄)-alkyl, where the heterocyclyl, heteroaryl                and aryl is unsubstituted or substituted by one or more                substituents selected from the group consisting of                halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl;        -   R⁹ is selected from the group consisting of hydrogen,            (C₁-C₁₂)-alkyl;        -   R¹⁰ is selected from the group consisting of            -   hydrogen;            -   aryl, heteroaryl, heterocyclyl, which is unsubstituted                or substituted by one or more substituents selected from                the group consisting of halogen, (C₁-C₆)-alkyl,                (C₁-C₆)-haloalkyl;            -   (C₃-C₇)-cycloalkyl-(C₁-C₄)-alkyl,                heterocyclyl-(C₁-C₄)-alkyl, heteroaryl-(C₁-C₄)-alkyl,                aryl-(C₁-C₄)-alkyl, aryl-(C₁-C₄)-alkoxy;            -   where the cycloalkyl, heterocyclyl, heteroaryl and aryl                is unsubstituted or substituted by one or more                substituents selected from the group consisting of                halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl;            -   (C₁-C₁₂)-alkyl; (C₃-C₈)-cycloalkyl, (C₂-C₁₂)-alkenyl,                (C₅-C₈)-cycloalkenyl, (C₂-C₁₂)-alkynyl;            -   where the abovementioned alkyl, cycloalkenyl, alkenyl,                cycloalkenyl and alkynyl radicals are unsubstituted or                each independently substituted by m radicals selected                from the group consisting of cyano, nitro, OR⁵,                S(O)_(n)R⁵, SO₂NR⁶R⁷, C(O)OR⁸, CONR⁶R⁸, COR⁶, NR⁶R⁸,                NR⁶COR⁸, NR⁶CONR⁸R⁸, NR⁶CO₂R⁸, NR⁶SO₂R⁸, NR⁶SO₂NR⁶R⁸,                C(R⁶)═NOR⁸;            -   (C₁-C₁₂)-haloalkyl;            -   S(O)_(n)R⁵, cyano, nitro, OR⁵, SO₂NR⁶R⁷, CO₂R⁸, COR⁸,                NR⁶R⁸, NR⁶COR⁸, NR⁶CO₂R⁸, NR⁶SO₂R⁸;                -   or        -   R⁹ and R¹⁰ together with the nitrogen atom to which they are            attached form a saturated, partially or fully unsaturated            five-, six- or seven-membered ring which is optionally mono-            to hexasubstituted by radicals from the group consisting of            halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, OR⁵, S(O)_(n)R⁵,            CO₂R⁸, CONR⁶R⁸, COR⁶ and C(R⁶)═NOR⁸ and which, in addition            to this nitrogen atom, contains r carbon atoms, o oxygen            atoms, p sulfur atoms and q elements from the group            consisting of NR⁷, CO and NCOR⁷ as ring atoms;        -   R⁵ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl            or aryl;        -   R⁶ is hydrogen or R⁵;        -   R⁷ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,            (C₃-C₄)-alkenyl or (C₃-C₄)-alkynyl;        -   R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,            (C₃-C₄)-alkenyl or (C₃-C₄)-alkynyl;

R^(2a) is selected from the group consisting of

-   -   hydrogen;    -   methyl;

R^(2b) is hydrogen;

R³ is selected from the group consisting of

-   -   halogen, cyano, isocyano, NO₂;    -   (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,        (C₁-C₄)-alkyloxycarbonyl;    -   (C₂-C₃)-alkenyl, (C₂-C₃)-haloalkenyl;    -   (C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl;    -   (C₁-C₂)-alkyl-S(O)_(n) and (C₁-C₂)-haloalkyl-S(O)_(n);    -   CHO;    -   NH₂;

R⁴ is a phenyl, where the phenyl radical is unsubstituted or mono- orpolysubstituted by a radical selected from the group consisting of

-   -   halogen, cyano, isocyano, nitro;    -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₃)-haloalkoxy;    -   (C₂-C₃)-alkenyl, (C₂-C₃)-haloalkenyl, (C₁-C₆)-alkoxy;    -   (C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl, (C₁-C₄)-alkyl-S(O)_(n);    -   CHO, (C₁-C₄)-alkyloxycarbonyl and NH₂;

R¹² is selected from the group consisting of

-   -   halogen, cyano, isocyano, NO₂;    -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-haloalkylcarbonyl, (C₁-C₄)-alkyloxycarbonyl,        (C₁-C₆)-alkoxy, (C₁-C₃)-haloalkoxy, (C₁-C₄)-alkyl-S(O)_(n);    -   (C₂-C₃)-alkenyl, (C₂-C₃)-haloalkenyl;    -   (C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl;    -   NH₂;

and where the indices are as follows:

m is 0, 1 or 2;

n is 0, 1 or 2;

o is 0, 1 or 2;

p is 0 or 1;

q is 0 or 1;

r is 3, 4, 5 or 6; and

s is 0, 1, 2, 3, 4 or 5, excluding the following compounds:

[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenylpyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.

Definitions

In the definitions of the symbols used in the formulae above, collectiveterms were used which generally represent the following substituents:

Halogen: fluorine, chlorine, bromine or iodine, preferably fluorine,chlorine or bromine, and more preferably fluorine or chlorine.

Alkyl: saturated straight-chain or branched hydrocarbon radical having 1to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, forexample (but not limited to) C₁-C₆-alkyl such as methyl, ethyl, propyl(n-propyl), 1-methylethyl (isopropyl), butyl (n-butyl), 1-methylpropyl(sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl),pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. This group is inparticular a C₁-C₄-alkyl group, e.g. a methyl, ethyl, propyl,1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl),2-methylpropyl (isobutyl) or 1,1-dimethylethyl (tert-butyl) group.Unless defined otherwise, for example for alkylsulfanyl, alkylsulfinyl,alkylsulfonyl, haloalkyl or haloalkylsulfanyl, this definition alsoapplies to alkyl as part of a composite substituent, for examplecycloalkylalkyl or hydroxyalkyl.

Alkenyl: unsaturated straight-chain or branched hydrocarbon groupshaving 2 to 8, preferably 2 to 6 and more preferably 2 to 4 carbon atomsand a double bond in any position, for example (but not limited to)C₂-C₆-alkenyl, such as vinyl, allyl, (E)-2-methylvinyl,(Z)-2-methylvinyl, isopropenyl, homoallyl, (E)-but-2-enyl,(Z)-but-2-enyl, (E)-but-1-enyl, (Z)-but-1-enyl, 2-methylprop-2-enyl,1-methylprop-2-enyl, 2-methylprop-1-enyl, (E)-1-methylprop-1-enyl,(Z)-1-methylprop-1-enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl,(E)-pent-2-enyl, (Z)-pent-2-enyl, (E)-pent-1-enyl, (Z)-pent-1-enyl,3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl,3-methylbut-2-enyl, (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl,(E)-1-methylbut-2-enyl, (Z)-1-methylbut-2-enyl, (E)-3-methylbut-1-enyl,(Z)-3-methylbut-1-enyl, (E)-2-methylbut-1-enyl, (Z)-2-methylbut-1-enyl,(E)-1-methylbut-1-enyl, (Z)-1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl,1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl,(E)-3,3-dimethylprop-1-enyl, (Z)-3,3-dimethylprop-1-enyl, hex-5-enyl,(E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl,(E)-hex-2-enyl, (Z)-hex-2-enyl, (E)-hex-1-enyl, (Z)-hex-1-enyl,4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl,1-methylpent-4-enyl, 4-methylpent-3-enyl, (E)-3-methylpent-3-enyl,(Z)-3-methylpent-3-enyl, (E)-2-methylpent-3-enyl,(Z)-2-methylpent-3-enyl, (E)-1-methylpent-3-enyl,(Z)-1-methylpent-3-enyl, (E)-4-methylpent-2-enyl,(Z)-4-methylpent-2-enyl, (E)-3-methylpent-2-enyl,(Z)-3-methylpent-2-enyl, (E)-2-methylpent-2-enyl,(Z)-2-methylpent-2-enyl, (E)-1-methylpent-2-enyl,(Z)-1-methylpent-2-enyl, (E)-4-methylpent-1-enyl,(Z)-4-methylpent-1-enyl, (E)-3-methylpent-1-enyl,(Z)-3-methylpent-1-enyl, (E)-2-methylpent-1-enyl,(Z)-2-methylpent-1-enyl, (E)-1-methylpent-1-enyl,(Z)-1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl,1-ethylbut-3-enyl, (E)-3-ethylbut-2-enyl, (Z)-3-ethylbut-2-enyl,(E)-2-ethylbut-2-enyl, (Z)-2-ethylbut-2-enyl, (E)-1-ethylbut-2-enyl,(Z)-1-ethylbut-2-enyl, (E)-3-ethylbut-1-enyl, (Z)-3-ethylbut-1-enyl,2-ethylbut-1-enyl, (E)-1-ethylbut-1-enyl, (Z)-1-ethylbut-1-enyl,2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl,1-isopropylprop-2-enyl, (E)-2-propylprop-1-enyl,(Z)-2-propylprop-1-enyl, (E)-1-propylprop-1-enyl,(Z)-1-propylprop-1-enyl, (E)-2-isopropylprop-1-enyl,(Z)-2-isopropylprop-1-enyl, (E)-1-isopropylprop-1-enyl,(Z)-1-isopropylprop-1-enyl, 1-(1,1-dimethylethyl)ethenyl,buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5-dienyl or methylhexadienyl.This group is in particular vinyl or allyl. Unless defined otherwise,this definition also applies to alkenyl as part of a compositesubstituent, for example haloalkenyl.

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 8,preferably 2 to 6 and more preferably 2 to 4 carbon atoms and a triplebond in any position, for example (but not limited to) C₂-C₆-alkynyl,such as ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl,but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl,pent-4-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl,3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, hex-1-ynyl, hex-2-ynyl,hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 3-methylpent-4-ynyl,2-methylpent-4-ynyl, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl,1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-2-ynyl,4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl,1-ethylbut-3-ynyl, 1-ethylbut-2-ynyl, 1-propylprop-2-ynyl,1-isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3-ynyl,1,1-dimethylbut-2-ynyl or 3,3-dimethylbut-1-ynyl. The alkynyl group isin particular ethynyl, prop-1-ynyl or prop-2-ynyl. Unless definedotherwise, this definition also applies to alkynyl as part of acomposite substituent, for example haloalkynyl.

Alkoxy: saturated straight-chain or branched alkoxy radicals having 1 to8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, forexample (but not limited to) C₁-C₆-alkoxy such as methoxy, ethoxy,propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy,1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy,3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, hexoxy, 1-methylpentoxy,2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy. Unless defined otherwise, this definitionalso applies to alkoxy as part of a composite substituent, for examplehaloalkoxy, alkynylalkoxy.

Alkoxycarbonyl: an alkoxy group which has 1 to 8, preferably 1 to 6 andmore preferably 1 to 4 carbon atoms (as specified above) and is bondedto the skeleton via a carbonyl group (—C(═O)—). Unless definedotherwise, this definition also applies to alkoxycarbonyl as part of acomposite substituent, for example cycloalkylalkoxycarbonyl.

Cycloalkyl: monocyclic, saturated hydrocarbyl groups having 3 to 10,preferably 3 to 8 and more preferably 3 to 6 carbon ring members, forexample (but not limited to) cyclopropyl, cyclopentyl and cyclohexyl.Unless defined otherwise, this definition also applies to cycloalkyl aspart of a composite substituent, for example cycloalkylalkyl.

Cycloalkenyl: monocyclic, partly unsaturated hydrocarbyl groups having 3to 10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members,for example (but not limited to) cyclopropenyl, cyclopentenyl andcyclohexenyl. Unless defined otherwise, this definition also applies tocycloalkenyl as part of a composite substituent, for examplecycloalkenylalkyl.

Cycloalkoxy: monocyclic, saturated cycloalkyloxy radicals having 3 to10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members,for example (but not limited to) cyclopropyloxy, cyclopentyloxy andcyclohexyloxy. Unless defined otherwise, this definition also applies tocycloalkoxy as part of a composite substituent, for examplecycloalkoxyalkyl.

Haloalkyl: straight-chain or branched alkyl groups having 1 to 8,preferably 1 to 6 and more preferably 1 to 4 carbon atoms (as describedabove), where some or all of the hydrogen atoms in these groups arereplaced by halogen atoms as described above, for example (but notlimited to) C₁-C₃-haloalkyl such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and1,1,1-trifluoroprop-2-yl. Unless defined otherwise, this definition alsoapplies to haloalkyl as part of a composite substituent, for examplehaloalkylaminoalkyl.

Haloalkenyl and haloalkynyl are defined analogously to haloalkyl, exceptthat, instead of alkyl groups, alkenyl and alkynyl groups, respectively,are present as part of the substituent.

Haloalkoxy: straight-chain or branched alkoxy groups having 1 to 8,preferably 1 to 6 and more preferably 1 to 4 carbon atoms (as describedabove), where some or all of the hydrogen atoms in these groups arereplaced by halogen atoms as described above, for example (but notlimited to) C₁-C₃-haloalkoxy such as chloromethoxy, bromomethoxy,dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy,2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxyand 1,1,1-trifluoroprop-2-oxy.

Unless defined otherwise, this definition also applies to haloalkoxy aspart of a composite substituent, for example haloalkoxyalkyl.

Aryl: mono-, bi- or tricyclic aromatic or partially aromatic grouphaving 6 to 14 carbon atoms, for example (but not limited to) phenyl,naphthyl, tetrahydronaphthyl, indenyl and indanyl. The bond to theparent general structure may be via any desired suitable ring member ofthe aryl radical. Aryl is preferably selected from phenyl, 1-naphthyland 2-naphthyl. Particular preference is given to phenyl.

Heteroaryl: 5- or 6-membered cyclic aromatic group having at least 1heteroatom, or else optionally 2, 3, 4 or 5 heteroatoms, where theheteroatoms are each independently selected from the group of S, N andO, where the group may also be part of a bi- or tricyclic system havingup to 14 ring members, where the ring system may be formed with one ortwo further cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/orheteroaryl radicals, and where benzofused 5- or 6-membered heteroarylgroups are preferred. The bonding to the parent general structure may bevia any desired suitable ring member of the heteroaryl radical. Examplesof 5-membered heteroaryl groups bonded to the skeleton via one of thecarbon ring members are fur-2-yl, fur-3-yl, thien-2-yl, thien-3-yl,pyrrol-2-yl, pyrrol-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-3-yl,pyrazol-4-yl, pyrazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, imidazol-2-yl, imidazol-4-yl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl,1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl. Examples of 5-memberedheteroaryl groups bonded to the skeleton via a nitrogen ring member arepyrrol-1-yl, pyrazol-1-yl, 1,2,4-triazol-1-yl, imidazol-1-yl,1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.

Examples of 6-membered heteroaryl groups are pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1,3,5-triazin-2-yl,1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl. Examples of benzofused5-membered heteroaryl groups are indol-1-yl, indol-2-yl, indol-3-yl,indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl,benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl,indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl,indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl,1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl,1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl,1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl,1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl,1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl,1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and1,3-benzoxazol-7-yl, Examples of benzofused 6-membered heteroaryl groupsare quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl,quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl,isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl,isoquinolin-7-yl and isoquinolin-8-yl. Further examples of 5- or6-membered heteroaryl radicals that are part of a bicyclic ring systemare 1,2,3,4-tetrahydroquinolin-1-yl, 1,2,3,4-tetrahydroquinolin-2-yl,1,2,3,4-tetrahydroquinolin-7-yl, 1,2,3,4-tetrahydroquinolin-8-yl,1,2,3,4-tetrahydroisoquinolin-1-yl, 1,2,3,4-tetrahydroisoquinolin-2-yl,1,2,3,4-tetrahydroisoquinolin-5-yl, 1,2,3,4-tetrahydroisoquinolin-6-yland 1,2,3,4-tetrahydroisoquinolin-7-yl. Unless defined otherwise, thisdefinition also applies to heteroaryl as part of a compositesubstituent, for example heteroarylalkyl.

Heterocyclyl: three- to seven-membered, saturated or partly unsaturatedheterocyclic group having at least one, optionally up to four,heteroatom(s) and/or hetero group(s) independently selected from thegroup consisting of N, O, S, S(═O), S(═O)₂ and di-(C₁-C₄)alkylsilyl,where the group may be benzofused. The bond to the parent generalstructure may be via a ring carbon atom or, if possible, via a ringnitrogen atom of the heterocyclic group. Saturated heterocyclic groupsin this context are, for example (but not limited to), oxiranyl,aziridinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-2-yl,pyrrolidin-3-yl, isoxazolidin-3-yl, isoxazolidin-4-yl,isoxazolidin-5-yl, isothiazolidin-3-yl, isothiazolidin-4-yl,isothiazolidin-5-yl, pyrazolidin-3-yl, pyrazolidin-4-yl,pyrazolidin-5-yl, oxazolidin-2-yl, oxazolidin-4-yl, oxazolidin-5-yl,thiazolidin-2-yl, thiazolidin-4-yl, thiazolidin-5-yl, imidazolidin-2-yl,imidazolidin-4-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,3,4-oxadiazolidin-2-yl, 1,2,4-thiadiazolidin-3-yl,1,2,4-thiadiazolidin-5-yl, 1,3,4-thiadiazolidin-2-yl,1,2,4-triazolidin-3-yl, 1,3,4-triazolidin-2-yl, piperidin-2-yl,piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-5-yl, tetrahydropyran-2-yl,tetrahydropyran-4-yl, tetrahydrothien-2-yl, hexahydropyridazin-3-yl,hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl,hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-2-yl,1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl. Partlyunsaturated heterocyclic groups in this context are, for example (butnot limited to), 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl,2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl.Examples of benzofused heterocyclic groups are indolin-1-yl,indolin-2-yl, indolin-3-yl, isoindolin-1-yl, isoindolin-2-yl,2,3-dihydrobenzofuran-2-yl and 2,3-dihydrobenzofuran-3-yl. Unlessdefined otherwise, this definition also applies to heterocyclyl as partof a composite substituent, for example heterocyclylalkyl.

Not included are combinations which contravene the laws of nature andwhich the person skilled in the art would therefore rule out on thebasis of their expert knowledge. For example, ring structures havingthree or more adjacent oxygen atoms are excluded.

Preference is given to compounds of the general formula (I) andagrochemically acceptable salts thereof where

A is selected from the group consisting of A1-A3,

R¹ is selected from the group consisting of

-   -   OR^(1a) and    -   NR⁹R¹⁰; where        -   R^(1a) is selected from the group consisting of            -   hydrogen;            -   methyl, ethyl which is unsubstituted or substituted by                one or more substituents selected from the group                consisting of halogen, (C₃-C₆)-cycloalkyl,                (C₁-C₄)-trialkylsilyl, (C₁-C₄)-alkoxy, cyano and nitro;            -   (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl;            -   aryl-(C₁-C₄)-alkyl, where the aryl is unsubstituted or                substituted by one or more substituents selected from                the group consisting of halogen, (C₁-C₄)-alkyl,                (C₁-C₄)-haloalkyl;        -   R⁹ is selected from the group consisting of hydrogen,            (C₁-C₆)-alkyl;        -   R¹⁰ is selected from the group consisting of            -   hydrogen;            -   (C₃-C₇)-cycloalkyl-(C₁-C₄)-alkyl, aryl-(C₁-C₄)-alkyl,                aryl-(C₁-C₄)-alkoxy,                -   where the cycloalkyl and aryl is unsubstituted or                    substituted by one or more substituents selected                    from the group consisting of halogen, (C₁-C₄)-alkyl,                    (C₁-C₄)-haloalkyl;            -   (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl;                (C₃-C₈)-cycloalkyl;                -   where the abovementioned alkyl, alkenyl, alkynyl and                    cycloalkenyl radicals are unsubstituted or are each                    independently substituted by m radicals selected                    from the group consisting of cyano, C(O)OR⁸;            -   (C₁-C₆)-haloalkyl        -   R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl;

R^(2a) is selected from the group consisting of

-   -   hydrogen;    -   methyl;

R^(2b) is hydrogen;

R³ is selected from the group consisting of

-   -   fluorine, chlorine, bromine, iodine, cyano, isocyano, NO₂;    -   (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl,        (C₁-C₄)-alkyloxycarbonyl;    -   (C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl;

R⁴ is phenyl, where the phenyl radical is unsubstituted or mono- orpolysubstituted by a radical selected from the group consisting of

-   -   fluorine, chlorine, bromine;    -   methyl, ethyl;    -   methoxy, ethoxy;

R¹² is selected from the group consisting of

-   -   halogen, cyano, nitro;    -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₃)-haloalkoxy;    -   (C₁-C₆)-alkoxy;

and where the indices are as follows:

m is 0, 1 or 2;

s is 0, 1, 2, 3,

excluding the compounds:

[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.

Particular preference is given to compounds of the general formula (I)and agrochemically acceptable salts thereof where

A is A1;

R¹ is selected from the group consisting of

-   -   OR^(1a) and    -   NR⁹R¹⁰; where        -   R^(1a) is selected from the group consisting of            -   hydrogen;            -   methyl, ethyl, trimethylsilylmethyl;            -   1-propenyl, 2-propenyl;            -   benzyl, 1-phenylethyl, 2-phenylethyl, where the phenyl                radical in each of the three groups mentioned is                unsubstituted or substituted by halogen;        -   R⁹ is hydrogen;        -   R¹⁰ is selected from the group consisting of            -   hydrogen;            -   cyclopropylmethyl;            -   benzyl, 1-phenylethyl, 2-phenylethyl, benzyloxy, where                the phenyl radical in each of the four groups mentioned                is unsubstituted or substituted by halogen;            -   methyl, ethyl, propyl, 1-methylethyl, butyl,                1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,                pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,                2,2-dimethylpropyl, 1-ethylpropyl, hexyl, where the                abovementioned radicals are unsubstituted or are each                independently monosubstituted by a C(O)OR⁸ radical;            -   cyclopropyl, cyclobutyl, cyclopentyl, where the three                radicals mentioned are unsubstituted or are each                independently monosubstituted by a C(O)OR⁸ radical;            -   1-propenyl, 2-propenyl, 2-methyl-2-propenyl,                prop-2-yn-1-yl, but-2-yn-1-yl;        -   R⁸ is hydrogen, methyl, ethyl;

R^(2a) is selected from the group consisting of

-   -   hydrogen;    -   methyl;

R^(2b) is hydrogen;

R³ is selected from the group consisting of

-   -   fluorine, chlorine, bromine, iodine, cyano, NO₂;    -   trifluoromethyl;    -   ethynyl;    -   C(O)Omethyl;

R⁴ is phenyl, where the phenyl radical is unsubstituted or mono- orpolysubstituted by a radical selected from the group consisting of

-   -   fluorine, chlorine, bromine;    -   methyl, ethyl;    -   methoxy, ethoxy;

R¹² is selected from the group consisting of

-   -   fluorine, chlorine, NO₂;    -   trifluoromethyl, methoxy, ethoxy;

and where the index is as follows:

s is 1, 2, 3,

excluding the compounds:

[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.

Very particular preference is given to compounds of the general formula(I) and agrochemically acceptable salts thereof where

A is A1

R¹ is selected from the group consisting of

-   -   OR^(1a) and    -   NR⁹R¹⁰; where        -   R^(1a) is selected from the group consisting of            -   hydrogen;            -   methyl, ethyl;            -   2-propenyl;        -   R⁹ is hydrogen;        -   R¹⁰ is selected from the group consisting of            -   cyclopentyl monosubstituted by C(O)OR^(B);            -   cyclopropylmethyl;            -   CH₂C(O)OR^(B), CH₂CH₂C(O)OR^(B);            -   2-propenyl, prop-2-yn-1-yl;        -   R⁸ is hydrogen, methyl, ethyl;

R^(2a) is selected from the group consisting of

-   -   hydrogen;    -   methyl;

R^(2b) is hydrogen;

R³ is selected from the group consisting of

-   -   chlorine, bromine, iodine, cyano, NO₂;

R⁴ is phenyl, where the phenyl radical is unsubstituted or mono- orpolysubstituted by a radical selected from the group consisting of

-   -   fluorine, chlorine;

R¹² is selected from the group consisting of

-   -   fluorine, chlorine;

and where the index is as follows:

s is 1, 2,

excluding the compounds:

[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.

The present compounds of the general formula (I) have, at the secondcarbon of the alkyl acid structure, a chiral carbon atom which, in thestructure shown below, is indicated by the marker (*):

According to the rules of Cahn, Ingold and Prelog (CIP rules), thiscarbon atom can have either an (R) configuration or an (S)configuration.

The present invention encompasses compounds of the general formula (I)both with (S) and with (R) configuration, meaning that the presentinvention encompasses the compounds of the general formula (I) in whichthe carbon atom in question has

(1) an (R) configuration; or

(2) an (S) configuration.

In addition, the scope of the present invention also encompasses

(3) any mixtures of compounds of the general formula (I) having an (R)configuration (compounds of the general formula (I-(R)) with compoundsof the general formula (I) having an (S) configuration (compounds of thegeneral formula (I-S)), the present invention also encompassing aracemic mixture of the compounds of the general formula (I) having (R)and (S) configuration.

However, within the context of the present invention, preference isgiven particularly to compounds of the general formula (I) having (R)configuration with a selectivity of 60 to 100%, preferably 80 to 100%,especially 90 to 100%, very particularly 95 to 100%, where theparticular (R) compound is present with an enantioselectivity of in eachcase more than 50% ee, preferably 60 to 100% ee, especially 80 to 100%ee, very particularly 90 to 100% ee, most preferably 95 to 100% ee,based on the total content of (R) compound in question.

Accordingly, the present invention relates especially to compounds ofthe general formula (I*) in which the stereochemical configuration onthe carbon atom marked by (*) is present with a stereochemical purity of60 to 100% (R), preferably 80 to 100% (R), especially 90 to 100% (R),very particularly 95 to 100% (R).

In addition, depending on the respective radicals chosen, furtherstereoelements may be present in the compounds of the general formula(I) according to the invention.

Preference is given to the compounds listed in the tables below. Thecompounds of the general formula (I) having (R) configuration are markedaccordingly in the column which lists the radical R^(2a). For example,if R^(2a)=alkyl, the preferred stereochemical configuration at thecarbon atom marked (*) of the general formula (I) is the (R)configuration.

Taking account of the Cahn, Ingold and Prelog rule, at the carbon atommarked by (*),

there may also be a situation in which, owing to the priority of thesubstituents in question, the (S) configuration is preferred at thecarbon atom marked by (*).

This is the case, for example, when the R^(2a) radical corresponds to a(C₁-C₆)-alkoxy radical.

Therefore, in the context of the present invention, preference is givenespecially to compounds of the general formula (I) that correspond interms of their spatial arrangement to those compounds of the generalformula (I) with R^(2a)=methyl having R configuration with a selectivityof 60% to 100%, preferably 80% to 100%, especially 90% to 100%, veryparticularly 95% to 100%, where

the respective (R) analogue compound is present with anenantioselectivity of more than 50% ee in each case,

preferably 60% to 100% ee, especially 80% to 100% ee, very particularly90% to 100% ee, most

preferably 95% to 100% ee, based on the total content of (R) analoguecompound in question.

Therefore, the present invention especially relates to compounds of thegeneral formula (I) in which the stereochemical configuration on thecarbon atom marked by (*) is present with a stereochemical purity of 60%to 100% (R or R analogue), preferably 80% to 100% (R or R analogue),especially 90% to 100% (R or R analogue), very particularly 95% to 100%(R or R analogue).

TABLE I Esters (I)

Ex. No. R¹ R^(2a) R^(2b) R³ R⁴ A I-001 MeO H H Cl 4-Cl—Ph Ph I-002 MeO HH Cl Ph 3-F—Ph I-003 MeO H H Cl 3-F—Ph 3-F—Ph I-004 MeO H H Cl Ph4-Cl—Ph I-005 MeO H H Cl 3-F—Ph 4-Cl—Ph I-006 MeO H H Cl 4-F—Ph 4-F—PhI-007 MeO H H Cl 4-Cl—Ph 4-F—Ph I-008 MeO H H Cl Ph 4-F—Ph I-009 MeO H HCN 4-F—Ph 4-F—Ph I-010 MeO H H CN 4-F—Ph 4-Cl—Ph I-011 MeO H H CN 4-F—PhPh I-012 MeO H H CN 3-F—Ph 4-F—Ph I-013 MeO H H CN 4-Cl—Ph 4-F—Ph I-014MeO H H CN Ph 4-F—Ph I-015 MeO H H Cl 2-F—Ph Ph I-016 MeO H H Cl 3-F—PhPh I-017 MeO H H CN 3-F—Ph 4-Cl—Ph I-018 MeO H H CN Ph 4-Cl—Ph I-019 MeOH H CN 4-MeO—Ph 3-F—Ph I-020 MeO H H CN 4-Me—Ph 3-F—Ph I-021 MeO H H CNPh 3-F—Ph I-022 MeO H H CN 2-F—Ph Ph I-023 MeO H H CN 3-F—Ph Ph I-024MeO H H CN 4-Cl—Ph Ph I-025 MeO H H Cl 4-F—Ph 3,4-diF—Ph I-026 MeO H HCl 3-ClPh 3,4-diF—Ph I-027 MeO H H Cl 3,4-diCl—Ph 3,4-diF—Ph I-028 MeO HH Cl Ph 4-EtO-3-F—Ph I-029 MeO H H Cl 4-Cl—Ph 3-F—Ph I-030 MeO H H Cl3-F—Ph 4-MeO—Ph I-031 MeO H H Cl 3-F—Ph 2,4-diCl—Ph I-032 MeO H H CN3-F—Ph 4-MeO—Ph I-033 MeO H H CN 4-Cl—Ph 4-MeO—Ph I-034 MeO H H CN Ph4-MeO—Ph I-035 MeO H H Cl 2,4-diCl—Ph 4-F—Ph I-036 MeO H H CN 4-F—Ph3,4-diF—Ph I-037 MeO H H CN 3-ClPh 4-MeO—Ph I-038 MeO H H CN 3-F—Ph3-ClPh I-039 MeO H H CN 4-MeO—Ph 3-ClPh I-040 MeO H H CN 4-Me—Ph 3-ClPhI-041 MeO H H CN 3-ClPh 4-Cl—Ph I-042 MeO H H CN 3-Cl-4-F—Ph4-EtO-3-F—Ph I-043 MeO H H CN 3-F—Ph 4-EtO-3-F—Ph I-044 MeO H H CN2,4-diCl—Ph 4-EtO-3-F—Ph I-045 MeO H H CN Ph 4-EtO-3-F—Ph I-046 MeO H HCN 3-ClPh 3-F—Ph I-047 MeO H H CN 3-F—Ph 3-F—Ph I-048 MeO H H CN 4-Cl—Ph3-F—Ph I-049 MeO H H CN 3-Cl-4-EtO—Ph 3-ClPh I-050 MeO H H CN3-Cl-4-EtO—Ph 4-Cl—Ph I-051 MeO H H CN 3-ClPh 3,4-diF—Ph I-052 MeO H HCF₃ Ph 4-F—Ph I-053 MeO (R)—Me H CF₃ Ph 4-F—Ph I-054 MeO H H Br 2-F—PhPh I-055 MeO H H Br 2-F—Ph 3,4-diF—Ph I-056 EtO H H Br Ph 4-F—Ph I-057OH H H Br Ph 4-F—Ph I-058 EtO H H I 2-F—Ph Ph I-059 EtO H H F 2-F—Ph PhI-060 EtO H H Cl 2-F—Ph Ph I-061 MeO Me H CN 2-F—Ph Ph I-062 MeO H HCO₂Me 2-F—Ph Ph I-063 MeO H H CCH 2-F—Ph Ph I-064 MeO Me H CN Ph 4-F—PhI-065 MeO H H CO₂Me Ph 4-F—Ph I-066 MeO H H CCH Ph 4-F—Ph I-067 MeO Me HCN 3-F—Ph 3-F—Ph I-068 MeO H H CO₂Me 3-F—Ph 3-F—Ph I-069 MeO H H CCH3-F—Ph 3-F—Ph I-070 EtO H H Br Ph Ph I-071 EtO H H Br Ph 4-Cl—Ph I-072EtO H H Br 4-F—Ph Ph I-073 EtO H H Br 4-Cl—Ph Ph I-074 EtO H H Br4-Cl—Ph 4-Cl—Ph I-075 EtO H H NO₂ 2-F—Ph Ph I-076 EtO H H Br 4-F—Ph4-F—Ph I-077 EtO H H Br 4-F—Ph 4-Cl—Ph I-078 EtO H H Br 4-Cl—Ph 4-F—PhI-079 EtO H H Br 2,4-diF—Ph Ph I-080 EtO H H Br 2,4-diF—Ph 4-Cl—Ph I-081EtO H H Br 2,4-diFPh 4-F—Ph I-082 OH H H Br 2-F—Ph Ph I-082 OH H H Br2-F—Ph Ph I-083 MeO H H Br 4-F—Ph 3-CF₃—Ph I-084 MeO H H Br 2-F—Ph2,3,4-triF—Ph I-085 EtO H H Br Ph 2,4-diF—Ph I-086 EtO H H Br 4-F—Ph2,4-diF—Ph I-087 EtO H H Br 4-Cl—Ph 2,4-diF—Ph I-088 EtO H H Br2,4-diF—Ph 2,4-diF—Ph I-089 EtO H H Br 2-MeO—Ph 4-F—Ph I-090 EtO H H Br2-MeO—Ph 4-Cl—Ph I-091 EtO H H Br 2-MeO—Ph 2,4-diF—Ph I-092 EtO H H Br2-MeO—Ph Ph I-093 EtO H H Cl 2,4,5-triF—Ph Ph I-094 MeO H H Cl 2-F—Ph5-F-2-Thienyl I-095 MeO H H Br 2-F—Ph 5-F-2-Thienyl I-096 OH H H Cl2,4,5-triF—Ph Ph I-097 EtO H H Cl 2,4,5-triF—Ph 3-F—Ph I-098 EtO H H Cl2,4-diF—Ph 3-F—Ph I-099 MeO H H NO₂ 2-F—Ph 4-NO₂—Ph I-100 EtO H H Cl2,4-diF—Ph Ph I-101 MeO H H Br Ph 4-F—Ph I-102 Me₃SiCH₂O H H Br 2-F—Ph3,4-diF—Ph I-103 OH Me H CN Ph 4-F—Ph I-104 MeO Me H CN 3-F—Ph 3-F—PhI-105 MeO Me H CN Ph 4-F—Ph I-106 OH Me H CN 3-F—Ph 3-F—Ph I-107 MeO H HBr 4-F—Ph 3-F—Ph I-108 MeO H H NO₂ 4-F—Ph 3-F—Ph I-109 MeO H H I 4-F—Ph3-F—Ph I-110 MeO H H Cl 4-F—Ph 3-F—Ph I-111 3-F—PhCH₂O H H Br Ph 4-F—PhI-112 PhCH₂O H H Br Ph 4-F—Ph I-113 CH₂═CHCH₂O H H Br Ph 4-F—Ph I-114MeO H H Br 3-F—Ph Ph I-115 MeO H H I 3-F—Ph Ph I-116 OH Me H CN Ph4-F—Ph I-117 OH Me H CN 3-F—Ph 3-F—Ph I-118 OH H H I 4-F—Ph 3-F—Ph I-119OH H H Br 4-F—Ph 3-F—Ph I-120 OH H H Cl 4-F—Ph 3-F—Ph I-121 OH H H NO₂4-F—Ph 3-F—Ph I-122 MeO H H NO₂ 3-F—Ph Ph I-123 3-F—PhCH₂O H H Br 4-F—Ph3-F—Ph I-124 PhCH₂O H H I 4-F—Ph 3-F—Ph I-125 MeO (R)—Me H CN 3-F—Ph3-F—Ph I-126 MeO (S)—Me H CN 3-F—Ph 3-F—Ph I-127 OH H H Br 3-F—Ph PhI-128 OH H H I 3-F—Ph Ph I-129 OH H H NO₂ 3-F—Ph Ph I-130 MeO (R)—Me HCN Ph 4-F—Ph I-131 EtO H H Cl 2-F—Ph 3,4-diF—Ph I-132 MeO Me H Br Ph4-F—Ph I-133 EtO H H Br 2-F—Ph 3,4-diF—Ph I-134 EtO H H Br 2,6-diF—Ph3,4-diF—Ph I-135 MeO Me Me Br Ph 4-F—Ph I-136 OH H H Br 2-F—Ph3,4-diF—Ph I-137 OH H H Br 2,6-diF—Ph 3,4-diF—Ph I-138 OH Me H Br Ph4-F—Ph I-139 OH Me H Cl Ph 4-F—Ph I-140 OH Me Me Br Ph 4-F—Ph I-141 MeO(S)—Me H CN Ph 4-F—Ph I-142 EtO H H Cl 2,6-diF—Ph 3,4-diF—Ph I-143 EtO HH NO₂ 2-F—Ph 3,4-diF—Ph I-144 EtO H H NO₂ 2,6-diF—Ph 3,4-diF—Ph I-145MeO Me H Cl Ph 4-F—Ph I-146 CH₂═CHCH₂O H H Cl 2,6-diF—Ph 3,4-diF—PhI-147 CH₂═CHCH₂O H H Cl 2-F—Ph 3,4-diF—Ph I-148 CH₂═CHCH₂O H H NO₂2-F—Ph 3,4-diF—Ph I-149 CH₂═CHCH₂O H H NO₂ 2,6-diF—Ph 3,4-diF—Ph I-150EtO H H Br 4-Cl-2-F—Ph 2,4-diF—Ph I-151 EtO H H Br 4-Cl-2-F—Ph4-Cl-2-F—Ph I-152 EtO H H Br 2,4-diCl—Ph 4-Cl-2-F—Ph I-153 EtO H H Br2,4-diClPh 2,4-diF—Ph I-154 EtO H H Br 4-Cl-2-F—Ph 2,4-diCl—Ph I-155 EtOH H Br 4-Cl-2-F—Ph 2-Cl-4-F—Ph I-156 EtO H H Br 4-Cl-2-F—Ph 4-F—Ph I-157EtO H H Br 4-Cl-2-F—Ph 4-Cl—Ph I-158 EtO H H Br 2,4-diCl—Ph 4-F—Ph I-159EtO H H Br 2,4-diCl—Ph 4-Cl—Ph I-160 EtO H H Br 4-F—Ph 4-Cl-2-F—Ph I-161EtO H H Br 4-Cl—Ph 4-Cl-2-F—Ph I-162 EtO H H Br 2-Cl-4-F—Ph 4-Cl-2-F—PhI-163 EtO H H Br 2,4-diF—Ph 4-Cl-2-F—Ph I-164 MeO Me H Cl Ph 3-F—PhI-165 MeO Me H Cl Ph 3,5-diF—Ph I-166 MeO Me H Cl Ph 2-F—Ph I-167 OH MeH Br 2,6-diF—Ph 3,4-diF—Ph I-168 OH Me H Br 2-F—Ph 3,4-diF—Ph I-169 MeOMe H Br 2,6-diF—Ph 3,4-diF—Ph I-170 MeO Me H Br 2-F—Ph 3,4-diF—Ph I-171MeO Me H CN 2-F—Ph 3,4-diF—Ph I-172 MeO (S)—Me H CN 2-F—Ph 3,4-diF—PhI-173 MeO (R)—Me H CN 2-F—Ph 3,4-diF—Ph I-174 MeO (R)—Me H Br 3-F—Ph PhI-175 OH (R)—Me H Br 3-F—Ph Ph I-176 MeO (S)—Me H Br 3-F—Ph Ph I-177 OH(S)—Me H Br 3-F—Ph Ph I-178 MeO (R)—Me H CN 2,6-diF—Ph 3,4-diF—Ph I-179MeO (S)—Me H CN 2,6-diF—Ph 3,4-diF—Ph I-180 EtO H H Br 2-F—Ph 2-F—PhI-181 MeO H H Br 2,5-diF—Ph 3,4-diF—Ph I-182 MeO (R)—Me H Br 2,5-diF—Ph3,4-diF—Ph I-183 MeO H H CN 2,5-diF—Ph 3,4-diF—Ph I-184 MeO (R)—Me H Br2-F—Ph 3,4-diF—Ph I-185 MeO (R)—Me H CN 2,5-diF—Ph 3,4-diF—Ph

TABLE II Salts (I)

Ex. No. M⁺ R^(2a) R^(2b) R³ R⁴ A II-01 K⁺ H H I 3-F—Ph Ph II-02 Na⁺ H HI 3-F—Ph Ph II-03 Li⁺ H H I 3-F—Ph Ph II-04 morpholin-4-ium H H I 3-F—PhPh II-05 2-propenylammonium H H I 3-F—Ph Ph II-06 propylammonium H H I3-F—Ph Ph II-07 tripropylammonium H H I 3-F—Ph Ph II-08ethyl(methyl)ammonium H H I 3-F—Ph Ph II-09 tert-butylammonium H H I3-F—Ph Ph II-10 2-phenylethylammonium H H I 3-F—Ph Ph II-11piperidin-1-ium H H I 3-F—Ph Ph II-12 octylammonium H H I 3-F—Ph PhII-13 benzylammonium H H I 3-F—Ph Ph II-14 triethylammonium H H I 3-F—PhPh

TABLE III Amides (I)

Ex. No. R¹ R^(2a) R^(2b) R³ R⁴ A III-001 2-methylprop-2-en-1-ylamino H HBr 2-F—Ph Ph III-002 cyclopropylamino H H Br 2-F—Ph Ph III-0032-propenylamino H H Br 2-F—Ph Ph III-004 2-propenylamino H H Br Ph4-F—Ph III-005 cyclopropylmethylamino H H Br Ph 4-F—Ph III-006prop-2-yn-1-ylamino H H Br Ph 4-F—Ph III-007 2-methylpropylamino H H BrPh 4-F—Ph III-008 2-propenylamino H H I 4-F—Ph 3-F—Ph III-009 butylaminoH H I 4-F—Ph 3-F—Ph III-010 benzylamino H H I 4-F—Ph 3-F—Ph III-011cyclopropylamino H H I 4-F—Ph 3-F—Ph III-012 cyclopropylmethylamino H HI 4-F—Ph 3-F—Ph III-013 2-methylpropylamino H H I 4-F—Ph 3-F—Ph III-0142-propenyl(methyl)amino H H I 4-F—Ph 3-F—Ph III-015 2-propenylamino H HBr 4-F—Ph 3-F—Ph III-016 prop-2-yn-1-ylamino H H Br 4-F—Ph 3-F—PhIII-017 but-2-yn-1-ylamino H H Br 4-F—Ph 3-F—Ph III-018 cyclopropylaminoH H Br 4-F—Ph 3-F—Ph III-019 (3-ethoxy-3-oxopropyl)amino H H Br 4-F—Ph3-F—Ph III-020 2-propenylamino Me H CN Ph 4-F—Ph III-021(3-methoxy-3-oxopropyl)amino Me H CN Ph 4-F—Ph III-022 2-propenylamino HH Cl 4-F—Ph 3-F—Ph III-023 prop-2-yn-1-ylamino H H Cl 4-F—Ph 3-F—PhIII-024 cyclopropylamino H H Cl 4-F—Ph 3-F—Ph III-025cyclopropylmethylamino H H Cl 4-F—Ph 3-F—Ph III-026(3-methoxy-3-oxopropyl)amino H H Cl 4-F—Ph 3-F—Ph III-027(2-methoxy-2-oxoethyl)amino H H Cl 4-F—Ph 3-F—Ph III-028cyclopropylamino H H NO₂ 4-F—Ph Ph III-029 (2-methoxy-2-oxoethyl)amino HH NO₂ 3-F—Ph Ph III-030 benzylamino H H NO₂ 3-F—Ph Ph III-0312-propenylamino H H NO₂ 3-F—Ph Ph III-032 2-phenylethylamino H H Br3-F—Ph Ph III-033 (3-ethoxy-3-oxopropyl)amino H H Br 3-F—Ph Ph III-034hexylamino H H Br 3-F—Ph Ph III-035 cyclopropylmethylamino H H Br 3-F—PhPh III-036 cyclopropylamino H H Br 3-F—Ph Ph III-037 2-propenylamino H HBr 3-F—Ph Ph III-038 benzyloxyamino H H I 3-F—Ph Ph III-039 pentylaminoH H NO₂ 4-F—Ph 3-F—Ph III-040 cyclopropylmethylamino H H NO₂ 4-F—Ph3-F—Ph III-041 cyclopropylamino H H NO₂ 4-F—Ph 3-F—Ph III-042prop-2-yn-1-ylamino H H NO₂ 4-F—Ph 3-F—Ph III-043 2-propenylamino H HNO₂ 4-F—Ph 3-F—Ph III-044 3,3,3-trifluoropropylamino H H Br 3-F—Ph3-F—Ph III-045 2-propenylamino Me H Br Ph 4-F—Ph III-046 propylamino MeH Br Ph 4-F—Ph III-047 cyclopropylmethylamino Me H Br Ph 4-F—Ph III-0482-methylpropylamino Me H Br Ph 4-F—Ph III-049 2-propenylamino Me H Cl Ph4-F—Ph III-050 propylamino Me H Cl Ph 4-F—Ph III-051cyclopropylmethylamino Me H Cl Ph 4-F—Ph III-052 2-methylpropylamino MeH Cl Ph 4-F—Ph III-053 2-propenylamino H H Br 2-F—Ph 3,4-diF—Ph III-0542-propenylamino H H Br 2,6-diF—Ph 3,4-diF—Ph III-055[3-(methoxycarbonyl)cyclopentyl]amino Me H Br Ph 4-F—Ph III-056(2-methoxy-2-oxoethyl)amino Me H Br Ph 4-F—Ph III-057(3-methoxy-3-oxopropyl)amino Me H Br Ph 4-F—Ph III-058(2-methoxy-2-oxoethyl)amino Me H Cl Ph 4-F—Ph III-059[3-(methoxycarbonyl)cyclopentyl]amino Me H Cl Ph 4-F—Ph III-060(3-methoxy-3-oxopropyl)amino Me H Cl Ph 4-F—Ph III-061(3-methoxy-3-oxopropyl)amino Me Me Br Ph 4-F—Ph III-062[3-(methoxycarbonyl)cyclopentyl]amino Me Me Br Ph 4-F—Ph III-0632-propenylamino Me Me Br Ph 4-F—Ph III-064 propylamino Me Me Br Ph4-F—Ph III-065 (2-methoxy-2-oxoethyl)amino Me Me Br Ph 4-F—Ph III-0662-propenylamino H H NO₂ 2-F—Ph 3,4-diF—Ph III-067 2-propenylamino H H Cl2-F—Ph 3,4-diF—Ph III-068 2-propenylamino H H Cl 2,6-diF—Ph 3,4-diF—PhIII-069 2-propenylamino H H NO₂ 2,6-diF—Ph 3,4-diF—Ph

A further aspect of the invention relates to the preparation of thecompounds of the general formula (I) according to the invention. Thecompounds according to the invention can be prepared in various ways.

Compounds according to the invention can be prepared, for example, bythe synthesis method shown in Scheme 1 below from substituted1,5-diphenyl-1H-pyrazol-3-ols or 1-phenyl-5-thienyl-1H-pyrazol-3-ols(II).

Scheme 1 describes the synthesis of the compound of the general formula(Ia, R³═Cl, Br, I) by reaction of a substituted pyrazole of the generalformula (IV) with an electrophilic halogenating reagent of the generalformula V, for example N-chlorosuccinimide (V, R³═Cl),N-bromosuccinimide (V, R³═Br) or N-iodosuccinimide (V, R³═I). In ananalogous manner, it is also possible to use other electrophilicreagents, for example electrophilic nitrating reagents such as nitratingacid, nitronium tetrafluoroborate or ammonium nitrate/trifluoroaceticacid (when R³═NO₂) or electrophilic fluorinating reagents, such as DAST,Selectfluor or N-fluorobenzenesulfonimide (when R³═F). The reactionpreferably takes place within the temperature range between 0° C. and120° C. in an appropriate solvent, for example N,N-dimethylformamide,1,2-dichloroethane or acetonitrile.

A compound of the general formula (Ib; R³═CN) can be prepared, forexample, by reaction of a compound of the formula (Ia; R³═Cl, Br, I,preferably R³═Br, I) in a suitable solvent with a metal cyanide M-CN (VIwith addition of a suitable amount of a transition metal catalyst,especially palladium catalysts such aspalladium(0)tetrakis(triphenylphosphine) or palladium diacetate orbis(triphenylphosphine)palladium(II) dichloride or nickel catalysts suchas nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II)chloride, preferably at elevated temperature in an organic solvent, forexample 1,2-dimethoxyethane or N,N-dimethylformamide. The “M” radicalrepresents, for example, magnesium, zinc, lithium or sodium.Cross-coupling methods that are suitable in general are those describedin R. D. Larsen, Organometallics in Process Chemistry 2004 SpringerVerlag, in I. Tsuji, Palladium Reagents and Catalysts 2004 Wiley, and inM. Belier, C. Bolm, Transition Metals for Organic Synthesis 2004VCH-Wiley. Further suitable synthesis methods are described in Chem.Rev. 2006, 106, 2651; Platinum Metals Review, 2009, 53, 183; PlatinumMetals Review 2008, 52, 172 and Acc. Chem. Res. 2008, 41, 1486.

The compound of the general formula (IV) can be prepared by alkylationof 3-hydroxypyrazoles of the general formula (II) with a halide of thegeneral formula (III) in the presence of a base, by or analogously tomethods known to the person skilled in the art. Preferably, the base isa carbonate salt of an alkali metal selected from the group consistingof lithium, sodium, potassium and caesium. The reaction preferably takesplace within the temperature range between room temperature and 150° C.in an appropriate solvent, for example dichloromethane, acetonitrile,N,N-dimethylformamide or ethyl acetate. See J. Med. Chem. 2011, 54(16),5820-5835 and WO2010/010154. The “X” radical represents, for example,chlorine, bromine or iodine.

The 3-hydroxypyrazoles (II) can be prepared, for example, analogously tomethods known from the literature in two stages from substituted3-phenyl- or thienylpropionic acid derivatives of the general formula(VII) (Scheme 2; see, for example: Adv. Synth. Catal. 2014, 356,3135-3147).

In the first step (Scheme 2), the compounds of the general formula (IX)are synthesized via an amide coupling of a substituted propionic acid ofthe general formula (VII) with an arylhydrazine of the general formula(VIII) in the presence of an amide coupling reagent, for examplepropanephosphonic anhydride (T3P), dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide,N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis,Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9).Polymer-bound reagents, for example polymer-bounddicyclohexylcarbodiimide, are also suitable for this coupling reaction.The reaction takes place preferably within the temperature range between0° C. and 80° C., in a suitable solvent, for example dichloromethane,tetrahydrofuran, acetonitrile, N,N-dimethylformamide or ethyl acetate,and in the presence of a base, for example triethylamine,N,N-diisopropylethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene (seeScheme 2). For T3P peptide coupling conditions see Organic ProcessResearch & Development 2009, 13, 900-906.

In the second step (Scheme 2), compounds of the general formula (IX) arecyclized in the presence of a couple halide, for example, copper(I)iodide, copper(I) bromide, or of a base such as sodium methoxide, or ofan acid such as methanesulfonic acid, to give 3-hydroxypyrazoles of thegeneral formula (II). The reaction preferably takes place in thetemperature range between 0° C. and 120° C. in a suitable solvent suchas 1,2-dichloroethane, acetonitrile, N,N-dimethylformamide, n-propanol,n-butanol or ethyl acetate.

The 3-hydroxypyrazoles (II) may also be prepared, for example, fromprotected 3-hydroxypyrazoles of the general formula (X). The protectinggroup R here is preferably a benzyl group or a trialkylsilyl group.

In the first step of Scheme 3, compounds of the general formula (XII)are prepared by an N-arylation of protected 3-hydroxypyrazoles of thegeneral formula (X) with an aryl halide of the general formula (XI) inthe presence of a copper halide, for example copper(I) iodide. Thereaction takes place preferably within the temperature range between 0°C. and 120° C., in an appropriate solvent, for example acetonitrile orN,N-dimethylformamide, and in the presence of a base, for exampletriethylamine or caesium carbonate. The compounds of the general formula(XII) can be prepared according to methods analogously known to theperson skilled in the art (e.g. Chem. Med. Chem. 2015, 10, 1184-1199).The “X” radical in compounds of the general formula (XI) is, forexample, chlorine, bromine or iodine.

In the second step, 5-iodopyrazoles of the general formula (XIII) areprepared from compounds of the general formula (XII). The reaction iseffected in the presence of a strong base, for example n-butyllithium orlithium diisopropylamide, and iodine. The reaction preferably takesplace within a temperature range between −78° C. and −60° C., in anappropriate solvent, for example diethyl ether or tetrahydrofuran.

A compound of the formula (XV) can be prepared, for example, by reactionof a compound of the formula (XIII) in a suitable solvent with acompound M-A (XIV) with addition of an appropriate amount of atransition metal catalyst, especially a palladium catalyst such aspalladium diacetate or bis(triphenylphosphine)palladium(II) dichloride,or a nickel catalyst such as nickel(II) acetylacetonate orbis(triphenylphosphine)nickel(II) chloride, preferably at elevatedtemperature in an organic solvent such as 1,2-dimethoxyethane. The “M”radical represents, for example, B(OR^(b))(OR^(c)), where the R^(b) andR^(c) radicals are independently, for example, hydrogen or(C₁-C₄)-alkyl, or, if the radicals R^(b) and R^(c) are bonded to oneanother, together are ethylene or propylene. Deprotecting a compound ofthe formula (XV) by standard methods that are well known to the personskilled in the art finally gives 3-hydroxypyrazoles of the generalformula (II) which can be converted further, for example as described inScheme 1, to the compounds according to the invention.

Compounds according to the invention can also be prepared, for example,by the synthesis method shown in Scheme 4 below from substituted5-amino-1-phenyl-1H-pyrazol-3-ols of the general formula (XVI).

Scheme 4 describes the synthesis of compounds of the formula (Ia) by oranalogously to methods known to the person skilled in the art, byreaction of a compound of the general formula (XIX) in which Hal ispreferably bromine or iodine, more preferably iodine, with a compoundM-A (XX) with addition of an appropriate amount of a transition metalcatalyst, especially a palladium catalyst such as palladium diacetate orbis(triphenylphosphine)palladium(II) dichloride, or a nickel catalystsuch as nickel(II) acetylacetonate or bis(triphenylphosphine)nickel(II)chloride, preferably at elevated temperature in an organic solvent suchas 1,2-dimethoxyethane or dioxane. The “M” radical represents, forexample, Mg-Hal, Zn-Hal, Sn((C₁-C₄)-alkyl)₃, lithium, copper orB(OR^(b))(OR^(c)), where the R^(b) and R^(c) radicals are independently,for example, hydrogen, (C₁-C₄)-alkyl, or, if the radicals R^(b) andR^(c) are bonded to one another, together are ethylene or propylene.

Compounds of the general formula (XIX) can be prepared by diazotizationand subsequent Sandmeyer reaction of 5-aminopyrazoles of the generalformula (XVIII) with the customary organic and inorganic nitrites, forexample 1,1-dimethylethyl nitrite, tert-butyl nitrite or isoamylnitrite, in the presence of usable reagents, for example mixtures ofcopper(I) and copper(II) bromide/chloride, iodine or diiodomethane(Scheme 4). The reaction preferably takes place within the temperaturerange between 0° C. and 120° C. in an appropriate solvent, for exampledichloromethane, acetonitrile or N,N-dimethylformamide.

The compound of the general formula (XVIII) is synthesized by oranalogously to methods known to the person skilled in the art, byreaction of a substituted pyrazole of the general formula (XVII) with anelectrophilic reagent, for example an electrophilic halogenating reagentsuch as N-chlorosuccinimide (when R³═Cl), N-bromosuccinimide (whenR³═Br), N-iodosuccinimide (when R³═I), or an electrophilic nitratingreagent such as nitrating acid, nitronium tetrafluoroborate, ammoniumnitrate/trifluoroacetic acid (when R³═NO₂), or an electrophilicfluorinating reagent, such as DAST, Selectfluor,N-fluorobenzenesulfonimide (when R³═F). The reaction preferably takesplace within the temperature range between 0° C. and 120° C. in anappropriate solvent, for example N,N-dimethylformamide,1,2-dichloroethane or acetonitrile. A compound of the general formula(XVIII; with R³═CN) can be prepared, for example, by reaction of acompound of the formula (XVIII; with R³=halogen, preferably R³═Br, I) ina suitable solvent with a metal cyanide, for example zinc cyanide, withaddition of a suitable amount of a transition metal catalyst, especiallypalladium catalysts such as palladium(0)tetrakis(triphenylphosphine) orpalladium diacetate or bis(triphenylphosphine)palladium(II) dichlorideor nickel catalysts such as nickel(II) acetylacetonate orbis(triphenylphosphine)nickel(II) chloride, preferably at elevatedtemperature in an organic solvent, for example 1,2-dimethoxyethane orN,N-dimethylformamide. Cross-coupling methods that are suitable ingeneral are those described in R. D. Larsen, Organometallics in ProcessChemistry 2004 Springer Verlag, in I. Tsuji, Palladium Reagents andCatalysts 2004 Wiley, and in M. Belier, C. Bolm, Transition Metals forOrganic Synthesis 2004 VCH-Wiley. Further suitable synthesis methods aredescribed in Chem. Rev. 2006, 106, 2651; Platinum Metals Review, 2009,53, 183; Platinum Metals Review 2008, 52, 172 and Acc. Chem. Res. 2008,41, 1486.

The compound of the general formula (XVII) can be synthesized byalkylation of substituted 5-amino-1-phenyl-1H-pyrazol-3-ols of thegeneral formula (XVI) with a halide of the general formula (III) in thepresence of a base, by or analogously to methods known to the personskilled in the art (see Scheme 4). The base may be a carbonate salt ofan alkali metal (for example lithium, sodium, potassium or caesium). Thereaction preferably takes place within the temperature range betweenroom temperature and 150° C. in an appropriate solvent, for exampledichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate.The “X” radical in the compound of the general formula (III) is, forexample, chlorine, bromine or iodine. The compounds of the generalformula (XVI) are commercially available or known from the literature.

The above-described compounds of the general formula (Ia) can be used toprepare, by the standard methods that are well known to the personskilled in the art, inventive compounds of the general formula (Ic) withR^(1a)═H, and (Id) with R¹═NR⁹R¹⁰.

As shown in Scheme 5, an acid of the general formula (Ic) can beprepared by hydrolysis of an ester of the general formula (Ia), by oranalogously to methods known to the person skilled in the art. Thehydrolysis can be carried out in the presence of a base or a Lewis acid.The base may be a hydroxide salt of an alkali metal (for examplelithium, sodium or potassium), and the hydrolysis reaction preferablytakes place within the temperature range between room temperature and120° C.

The inventive compounds of the general formula (Id) are synthesized, forexample, via an amide coupling of an acid of the general formula (Ic)with an amine of the general formula (XXI) in the presence of an amidecoupling reagent, for example propanephosphonic anhydride (T3P),dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide,N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide (see Chemistry of Peptide Synthesis,Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9).Polymer-bound reagents, for example polymer-bounddicyclohexylcarbodiimide, are also suitable for this coupling reaction.The reaction takes place preferably within the temperature range between0° C. and 80° C., in a suitable solvent, for example dichloromethane,acetonitrile, N,N-dimethylformamide or ethyl acetate, and in thepresence of a base, for example triethylamine, N,N-diisopropylethylamineor 1,8-diazabicyclo[5.4.0]undec-7-ene. For T3P peptide couplingconditions see Organic Process Research & Development 2009, 13, 900-906.

The inventive compounds of the formula (I) (and/or salts thereof),referred to collectively as “compounds of the invention” hereinafter,have excellent herbicidal efficacy against a broad spectrum ofeconomically important monocotyledonous and dicotyledonous annualharmful plants.

The present invention therefore also provides a method for controllingunwanted plants or for regulating the growth of plants, preferably inplant crops, in which one or more compound(s) of the invention is/areapplied to the plants (for example harmful plants such asmonocotyledonous or dicotyledonous weeds or unwanted crop plants), theseed (for example grains, seeds or vegetative propagules such as tubersor shoot parts with buds) or the area on which the plants grow (forexample the area under cultivation). The compounds of the invention canbe deployed, for example, prior to sowing (if appropriate also byincorporation into the soil), prior to emergence or after emergence.Specific examples of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compounds ofthe invention are as follows, though the enumeration is not intended toimpose a restriction to particular species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

When the compounds of the invention are applied to the soil surfacebefore germination, either the weed seedlings are prevented completelyfrom emerging or the weeds grow until they have reached the cotyledonstage, but then stop growing.

If the active ingredients are applied post-emergence to the green partsof the plants, growth stops after the treatment, and the harmful plantsremain at the growth stage at the time of application, or they diecompletely after a certain time, so that in this manner competition bythe weeds, which is harmful to the crop plants, is eliminated very earlyand in a sustained manner.

The compounds of the invention can be selective in crops of usefulplants and can also be employed as non-selective herbicides.

By virtue of their herbicidal and plant growth regulatory properties,the active ingredients can also be used to control harmful plants incrops of genetically modified plants which are known or are yet to bedeveloped. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain active ingredients used in the agrochemical industry, inparticular certain herbicides, resistances to plant diseases orpathogens of plant diseases, such as certain insects or microorganismssuch as fungi, bacteria or viruses. Other specific characteristicsrelate, for example, to the harvested material with regard to quantity,quality, storability, composition and specific constituents. Forinstance, there are known transgenic plants with an elevated starchcontent or altered starch quality, or those with a different fatty acidcomposition in the harvested material. Further particular properties liein tolerance or resistance to abiotic stress factors, for example heat,cold, drought, salinity and ultraviolet radiation.

Preference is given to using the inventive compounds of the formula (I)or salts thereof in economically important transgenic crops of usefuland ornamental plants.

The compounds of the formula (I) can be used as herbicides in crops ofuseful plants which are resistant, or have been made resistant bygenetic engineering, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional cultivation methods and the generation of mutants.Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods (see, for example, EP 0221044, EP0131624). What has been described are, for example, several cases ofgenetic modifications of crop plants for the purpose of modifying thestarch synthesized in the plants (e.g. WO 92/011376 A, WO 92/014827 A,WO 91/019806 A), transgenic crop plants which are resistant to certainherbicides of the glufosinate type (cf., for example, EP 0242236 A, EP0242246 A) or of the glyphosate type (WO 92/000377 A) or of thesulfonylurea type (EP 0257993 A, U.S. Pat. No. 5,013,659) or tocombinations or mixtures of these herbicides through “gene stacking”,such as transgenic crop plants, for example maize or soya with the tradename or the designation Optimum™ GAT™ (Glyphosate ALS Tolerant),

-   -   transgenic crop plants, for example cotton, capable of producing        Bacillus thuringiensis toxins (Bt toxins), which make the plants        resistant to particular pests (EP 0142924 A, EP 0193259 A),    -   transgenic crop plants having a modified fatty acid composition        (WO 91/013972 A),    -   genetically modified crop plants having novel constituents or        secondary metabolites, for example novel phytoalexins, which        cause an increase in disease resistance (EP 0309862 A, EP        0464461 A)    -   genetically modified plants having reduced photorespiration,        which have higher yields and higher stress tolerance (EP 0305398        A)    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”)    -   transgenic crop plants which feature higher yields or better        quality    -   transgenic crop plants which are distinguished by a combination,        for example of the abovementioned novel properties (“gene        stacking”).

Numerous molecular biology techniques which can be used to produce noveltransgenic plants with modified properties are known in principle; see,for example, I. Potrykus and G. Spangenberg (eds), Gene Transfer toPlants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelbergor Christou, “Trends in Plant Science” 1 (1996) 423-431).

For such genetic manipulations, nucleic acid molecules which allowmutagenesis or sequence alteration by recombination of DNA sequences canbe introduced into plasmids. With the aid of standard methods, it ispossible, for example, to undertake base exchanges, remove partsequences or add natural or synthetic sequences. For the connection ofthe DNA fragments to one another, it is possible to add adapters orlinkers to the fragments; see, for example, Sambrook et al., 1989,Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring HarborLaboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene undKlone” [Genes and Clones], VCH Weinheim, 2nd edition, 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis firstly possible to use DNA molecules which encompass the entirecoding sequence of a gene product inclusive of any flanking sequenceswhich may be present, and also DNA molecules which only encompassportions of the coding sequence, in which case it is necessary for theseportions to be long enough to have an antisense effect in the cells. Itis also possible to use DNA sequences which have a high degree ofhomology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants. Obtainable in this way are transgenic plantshaving properties altered by overexpression, suppression or inhibitionof homologous (=natural) genes or gene sequences or expression ofheterologous (=foreign) genes or gene sequences.

The compounds (I) of the invention can be used with preference intransgenic crops which are resistant to growth regulators, for example2,4-D, dicamba, or to herbicides which inhibit essential plant enzymes,for example acetolactate synthases (ALS), EPSP synthases, glutaminesynthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or toherbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active ingredients, orto any desired combinations of these active ingredients.

The compounds of the invention can be used with particular preference intransgenic crop plants which are resistant to a combination ofglyphosates and glufosinates, glyphosates and sulfonylureas orimidazolinones. Most preferably, the compounds of the invention can beused in transgenic crop plants such as maize or soya with the trade nameor the designation Optimum™ GAT™ (glyphosate ALS tolerant), for example.

When the active ingredients of the invention are employed in transgeniccrops, not only do the effects towards harmful plants observed in othercrops occur, but frequently also effects which are specific to theapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also relates to the use of the inventivecompounds of the formula (I) as herbicides for controlling harmfulplants in transgenic crop plants.

The compounds of the invention can be applied in the form of wettablepowders, emulsifiable concentrates, sprayable solutions, dustingproducts or granules in the customary formulations. The inventiontherefore also provides herbicidal and plant-growth-regulatingcompositions which comprise the compounds of the invention.

The compounds of the invention can be formulated in various ways,according to the biological and/or physicochemical parameters required.Possible formulations include, for example: wettable powders (WP),water-soluble powders (SP), water-soluble concentrates, emulsifiableconcentrates (EC), emulsions (EW), such as oil-in-water and water-in-oilemulsions, sprayable solutions, suspension concentrates (SC),dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), dressings, granules forscattering and soil application, granules (GR) in the form ofmicrogranules, spray granules, absorption and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes. These individual formulationtypes are known in principle and are described, for example, in:Winnacker-Kuchler, “Chemische Technologie” [Chemical Technology], Volume7, C. Hanser Verlag Munich, 4th Ed. 1986, Wade van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y., 1973, K. Martens, “SprayDrying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials,surfactants, solvents and further additives are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley &Sons, N.Y., C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y.1963, McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J., Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964, Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler,“Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed.1986.

On the basis of these formulations, it is also possible to producecombinations with other active ingredients, for example insecticides,acaricides, herbicides, fungicides, and also with safeners, fertilizersand/or growth regulators, for example in the form of a finishedformulation or as a tank mix.

Combination partners usable for the compounds of the invention in mixedformulations or in a tankmix are, for example, known active ingredientsbased on inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoene desaturase, photosystem I, photosystem II or protoporphyrinogenoxidase, as known, for example, from Weed Research 26 (1986) 441-445 or“The Pesticide Manual”, 16th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2006, and literature citedtherein. Known herbicides or plant growth regulators which can becombined with the compounds of the invention are, for example, thefollowing, where said active ingredients are referred to either by their“common name” in accordance with the International Organization forStandardization (ISO) or by the chemical name or by the code number.They always encompass all the use forms, for example acids, salts,esters and also all isomeric forms such as stereoisomers and opticalisomers, even if they are not mentioned explicitly.

Examples of such herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor,allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone,amidochlor, amidosulfuron,4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylicacid, aminocyclopyrachlor, aminocyclopyrachlor-potassium,aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate,anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid,benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac,bispyribac-sodium, bixlozone, bromacil, bromobutide, bromofenoxim,bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate,busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin,butroxydim, butylate, cafenstrole, carbetamide, carfentrazone,carfentrazone-ethyl, chloramben, chlorbromuron,1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one,4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1,3-dimethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate,chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol,chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl,2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one,4-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}-1-ethyl-1H-pyrazol-5-yl1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorophthalim, chlorotoluron,chlorthal-dimethyl, chlorsulfuron,3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one,cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim,clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid,cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine,cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim,cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl,-dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl,-isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and-trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl,-potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol,desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil,dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr,diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimethenamid-P,3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione,1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-yl1,3-dimethyl-1H-pyrazole-4-carboxylate, dimetrasulfuron, dinitramine,dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DMPA,DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron,ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen,ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, ethyl[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate,F-9960, F-5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide,F-7967, i.e.3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl,fenoxasulfone, fenquinotrione, fentrazamide, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-P,fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron,flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen,fluoroglycofen-ethyl, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr,fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen,fomesafen-sodium, foramsulfuron, fosamine, glufosinate,glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium,glufosinate-P-sodium, glyphosate, glyphosate-ammonium,-isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodiumand -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen,halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate,4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one,4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one,(5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanone,6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione,imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium,imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium,imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium,imazosulfuron, indanofan, indaziflam, iodosulfuron,iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium andsodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole,karbutilate, KUH-043, i.e.3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl,-dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and-sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop,mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl,-dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide,mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron,metam, metamifop, metamitron, metazachlor, metazosulfuron,methabenzthiazuron, methiopyrsulfuron, methiozolin,2-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)cyclohexane-1,3-dione,methyl isothiocyanate,1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate, metobromuron, metolachlor, S-metolachlor,metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl,molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e.N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011,napropamide, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid(fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione),oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin,penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils,phenmedipham, picloram, picolinafen, pinoxaden, piperophos,pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine,profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop,propazine, propham, propisochlor, propoxycarbazone,propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb,prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole,pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl,pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl,pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid,pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM-201, QYR-301, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrion,sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,terbumeton, terbuthylazin, terbutryn, tetflupyrolimet, thenylchlor,thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate,topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron,triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine,trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin,triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate,vernolate, ZJ-0862, i.e.3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline.

Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol,6-benzylaminopurine, brassinolide, catechol, chlormequat chloride,cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide,dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal,endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium),ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol,forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid(IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonicacid, jasmonic acid methyl ester, maleic hydrazide, mepiquat chloride,1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid,2-naphthyloxyacetic acid, nitrophenolate mixture,4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazole,N-phenylphthalamic acid, prohexadione, prohexadione-calcium,prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron,triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole,uniconazole-P.

Safeners which can be used in combination with the inventive compoundsof the formula (I) and optionally in combinations with further activecompounds such as insecticides, acaricides, herbicides, fungicides aslisted above are preferably selected from the group consisting of:

S1) Compounds of the formula (S1)

where the symbols and indices are defined as follows:

n_(A) is a natural number from 0 to 5, preferably from 0 to 3;

R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or(C₁-C₄)-haloalkyl;

W_(A) is an unsubstituted or substituted divalent heterocyclic radicalfrom the group of the partly unsaturated or aromatic five-memberedheterocycles having 1 to 3 ring heteroatoms from the N and O group,where at least one nitrogen atom and at most one oxygen atom is presentin the ring, preferably a radical from the group of (W_(A) ¹) to (W_(A)⁴),

m_(A) is 0 or 1;

R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated orunsaturated 3- to 7-membered heterocycle having at least one nitrogenatom and up to 3 heteroatoms, preferably from the group consisting of Oand S, which is joined to the carbonyl group in (S1) via the nitrogenatom and is unsubstituted or substituted by radicals from the groupconsisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally substitutedphenyl, preferably a radical of the formula OR_(A) ³, NHR_(A) ⁴ orN(CH₃)₂, especially of the formula OR_(A) ³;

R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatichydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;

R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted orunsubstituted phenyl;

R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,(C₁-C₄)-alkoxy-(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹, where R_(A) ⁹ ishydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl, (C₃-C₁₂)-cycloalkylor tri-(C₁-C₄)-alkylsilyl;

R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are hydrogen,(C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl or substituted orunsubstituted phenyl;

preferably:

a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type(S1^(a)), preferably compounds such as1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylicacid, ethyl1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate(S1-1) (“mefenpyr-diethyl”), and related compounds as described inWO-A-91/07874;

b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1^(b)),preferably compounds such as ethyl1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate(S1-4) and related compounds as described in EP-A-333 131 and EP-A-269806;

c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1^(c)),preferably compounds such as ethyl1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and relatedcompounds as described in EP-A-268 554, for example;

d) compounds of the triazolecarboxylic acid type (S1^(d)), preferablycompounds such as fenchlorazole(-ethyl ester), i.e. ethyl1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate(S1-7), and related compounds as described in EP-A-174 562 and EP-A-346620;

e) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylicacid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type(S1^(e)), preferably compounds such as ethyl5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds asdescribed in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylicacid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11)(“isoxadifen-ethyl”) or n-propyl5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), asdescribed in patent application WO-A-95/07897.

S2) Quinoline derivatives of the formula (S2)

where the symbols and indices have the meanings below:

R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or(C₁-C₄)-haloalkyl;

n_(B) is a natural number from 0 to 5, preferably from 0 to 3;

R_(B) ² is OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated

or unsaturated 3- to 7-membered heterocycle having at least one nitrogenatom and up to 3 heteroatoms, preferably from the group of O and S,which is joined via the nitrogen atom to the carbonyl group in (S2) andis unsubstituted or substituted by radicals from the group of(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally substituted phenyl,preferably a radical of the formula OR_(B) ³, NHR_(B) ⁴ or N(CH₃)₂,especially of the formula OR_(B) ³;

R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatichydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;

R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted orunsubstituted phenyl;

T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted orsubstituted by one or two (C₁-C₄)-alkyl radicals or by[(C₁-C₃)-alkoxy]carbonyl;

preferably:

a) compounds of the 8-quinolinoxyacetic acid type (S2^(a)), preferably

-   1-methylhexyl (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”)    (S2-1),-   (1,3-dimethylbut-1-yl) (5-chloro-8-quinolinoxy)acetate (S2-2),-   4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),-   1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4),-   ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),-   methyl (5-chloro-8-quinolinoxy)acetate (S2-6),-   allyl (5-chloro-8-quinolinoxy)acetate (S2-7),-   2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate    (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and    related compounds, as described in EP-A-86 750, EP-A-94 349 and    EP-A-191 736 or EP-A-0 492 366, and also    (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts    thereof, for example the lithium, sodium, potassium, calcium,    magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium    or phosphonium salts thereof, as described in WO-A-2002/34048;

b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2^(b)),preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate,diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl(5-chloro-8-quinolinoxy)malonate and related compounds, as described inEP-A-0 582 198.

S3) Compounds of the formula (S3)

where the symbols and indices are defined as follows:

R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl;

R_(C) ², R_(C) ³ are identical or different and are hydrogen,(C₁-C₄)alkyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,(C₂-C₄)haloalkenyl, (C₁-C₄)alkylcarbamoyl-(C₁-C₄)alkyl,(C₂-C₄)alkenylcarbamoyl-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,dioxolanyl-(C₁-C₄)alkyl, thiazolyl, furyl, furylalkyl, thienyl,piperidyl, substituted or unsubstituted phenyl, or R_(C) ² and R_(C) ³together form a substituted or unsubstituted heterocyclic ring,preferably an oxazolidine, thiazolidine, piperidine, morpholine,hexahydropyrimidine or benzoxazine ring;

preferably:

-   -   active compounds of the dichloroacetamide type, which are        frequently used as pre-emergence safeners (soil-acting        safeners), for example

-   “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),

-   “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from    Stauffer (S3-2),

-   “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from    Stauffer (S3-3),

-   “benoxacor”    (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),

-   “PPG-1292” (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide)    from PPG Industries (S3-5),

-   “DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide)    from Sagro-Chem (53-6),

-   “AD-67” or “MON 4660” (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane)    from Nitrokemia or Monsanto (53-7),

-   “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (53-8),

-   “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (53-9)

-   ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one)    from BASF,

-   “furilazole” or “MON 13900”    ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (53-10);    and the (R) isomer thereof (S3-11).

S4) N-acylsulfonamides of the formula (S4) and salts thereof,

in which the symbols and indices are defined as follows:

A_(D) is SO₂—NR_(D) ³—CO or CO—NR_(D) ³—SO₂

X_(D) is CH or N;

R_(D) ¹ is CO—NR_(D) ⁵R_(D) ⁶ or NHCO—R_(D) ⁷;

R_(D) ² is halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, nitro,(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;

R_(D) ³ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or (C₂-C₄)-alkynyl;

R_(D) ⁴ is halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy, cyano,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;

R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl, phenyl or 3- to 6-memberedheterocyclyl containing v_(D) heteroatoms from the group consisting ofnitrogen, oxygen and sulfur, where the seven latter radicals aresubstituted by v_(D) substituents from the group consisting of halogen,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₂)-alkylsulfinyl,(C₁-C₂)-alkylsulfonyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkylcarbonyl and phenyl and, in the case of cyclic radicals,also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;

R_(D) ⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,where the three latter radicals are substituted by v_(D) radicals fromthe group consisting of halogen, hydroxyl, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxyand (C₁-C₄)-alkylthio, or

R_(D) ⁵ and R_(D) ⁶ together with the nitrogen atom carrying them form apyrrolidinyl or piperidinyl radical;

R_(D) ⁷ is hydrogen, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 latter radicals aresubstituted by v_(D) substituents from the group consisting of halogen,(C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy and (C₁-C₄)-alkylthio and, in thecase of cyclic radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;

n_(D) is 0, 1 or 2;

m_(D) is 1 or 2;

v_(D) is 0, 1, 2 or 3;

among these, preference is given to compounds of the N-acylsulfonamidetype, for example of the formula (S4a) below, which are known, forexample, from WO-A-97/45016

in which

R_(D) ⁷ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 latterradicals are substituted by v_(D) substituents from the group consistingof halogen, (C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy and (C₁-C₄)-alkylthioand, in the case of cyclic radicals, also (C₁-C₄)-alkyl and(C₁-C₄)-haloalkyl;

R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;

m_(D) is 1 or 2;

v_(D) is 0, 1, 2 or 3;

and also

acylsulfamoylbenzamides, for example of the formula (S4^(b)) below,which are known, for example, from WO-A-99/16744,

e.g. those in which

R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=2-OMe (“cyprosulfamide”, S4-1),

R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-2),

R_(D) ⁵=ethyl and (R_(D) ⁴)=2-OMe (S4-3),

R_(D) ⁵=isopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-4) and

R_(D) ⁵=isopropyl and (R_(D) ⁴)=2-OMe (S4-5)

and also

compounds of the N-acylsulfamoylphenylurea type of the formula (S4^(c)),which are known, for example, from EP-A-365484,

in which

R_(D) ⁸ and R_(D) ⁹ independently represent hydrogen, (C₁-C₈)-alkyl,(C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,

R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃,

m_(D) is 1 or 2;

for example

-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,-   1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,    and also

N-phenylsulfonylterephthalamides of the formula (S4^(d)), which areknown, for example, from CN 101838227,

e.g. those in which

R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;

m_(D) is 1 or 2;

R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl.

S5) Active ingredients from the class of the hydroxyaromatics and thearomatic-aliphatic carboxylic acid derivatives (S5), for example

ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid,3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylicacid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described inWO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.

S6) Active ingredients from the class of the1,2-dihydroquinoxalin-2-ones (S6), for example

1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-onehydrochloride,1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,as described in WO-A-2005/112630.

S7) Compounds of the formula (S7), as described in WO-A-1998/38856,

in which the symbols and indices are defined as follows:

R_(E) ¹, R_(E) ² are independently halogen, (C₁-C₄)-alkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkylamino,di-(C₁-C₄)-alkylamino, nitro;

A_(E) is COOR_(E) ³ or COSR_(E) ⁴

R_(E) ³, R_(E) ⁴ are independently hydrogen, (C₁-C₄)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl, (C₁-C₄)-haloalkyl, phenyl,nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium,

n_(E) ¹ is 0 or 1

n_(E) ², n_(E) ³ are independently 0, 1 or 2,

preferably:

diphenylmethoxyacetic acid,

ethyl diphenylmethoxyacetate,

methyl diphenylmethoxyacetate (CAS reg. no. 41858-19-9) (S7-1).

S8) Compounds of the formula (S8), as described in WO-A-98/27049,

in which

X_(E) is CH or N,

n_(E) in the case that X_(E)═N is an integer from 0 to 4 and

-   -   in the case that X_(F)═CH is an integer from 0 to 5,

R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-alkoxycarbonyl, optionally substituted phenyl, optionallysubstituted phenoxy,

R_(F) ² is hydrogen or (C₁-C₄)-alkyl,

R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl oraryl, where each of the abovementioned carbon-containing radicals isunsubstituted or substituted by one or more, preferably up to threeidentical or different radicals from the group consisting of halogen andalkoxy; or salts thereof,

preferably compounds in which

X_(F) is CH,

n_(F) is an integer from 0 to 2,

R^(F) is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy,

R_(F) ² is hydrogen or (C₁-C₄)-alkyl,

R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl oraryl, where each of the abovementioned carbon-containing radicals isunsubstituted or substituted by one or more, preferably up to threeidentical or different radicals from the group consisting of halogen andalkoxy,

or salts thereof.

S9) Active ingredients from the class of the3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example

1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CASreg. no. 219479-18-2),1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CASReg. No. 95855-00-8), as described in WO-A-1999/000020.

S10) Compounds of the formulae (S10a) or (S10^(b))

-   -   as described in WO-A-2007/023719 and WO-A-2007/023764

in which

R_(G) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃,

Y_(G), Z_(G) independently of one another represent O or S,

n_(G) is an integer from 0 to 4,

R_(G) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl, aryl;benzyl, halobenzyl,

R_(G) ³ is hydrogen or (C₁-C₆)-alkyl.

S11) Active ingredients of the oxyimino compounds type (S11), which areknown as seed-dressing agents, for example

“oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile)(S11-1), which is known as a seed-dressing safener for millet/sorghumagainst metolachlor damage,

“fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanoneO-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as aseed-dressing safener for millet/sorghum against metolachlor damage, and

“cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile)(S11-3), which is known as a seed-dressing safener for millet/sorghumagainst metolachlor damage.

S12) Active ingredients from the class of the isothiochromanones (S12),for example methyl[(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No.205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.

S13) One or more compounds from group (S13):

“naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1),which is known as a seed-dressing safener for maize againstthiocarbamate herbicide damage,

“fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known asa safener for pretilachlor in sown rice,

“flurazole” (benzyl2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which isknown as a seed-dressing safener for millet/sorghum against alachlor andmetolachlor damage,

“CL 304415” (CAS Reg. No. 31541-57-8)

(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) fromAmerican Cyanamid, which is known as a safener for maize against damageby imidazolinones,

“MG 191” (CAS Reg. No. 96420-72-3)(2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, whichis known as a safener for maize,

“MG 838” (CAS Reg. No. 133993-74-5)

(2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) fromNitrokemia,

“disulfoton” (O,O-diethyl S-2-ethylthioethyl phosphorodithioate)(S13-7),

“dietholate” (O,O-diethyl O-phenyl phosphorothioate) (S13-8),

“mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

S14) Active ingredients which, in addition to herbicidal action againstharmful plants, also have safener action on crop plants such as rice,for example

“dimepiperate” or “MY 93” (S-1-methyl1-phenylethylpiperidine-1-carbothioate), which is known as a safener forrice against damage by the herbicide molinate,

“daimuron” or “SK 23” (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), whichis known as a safener for rice against damage by the herbicideimazosulfuron,

“cumyluron”=“JC 940”(3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, seeJP-A-60087254), which is known as safener for rice against damage bysome herbicides,

“methoxyphenone” or “NK 049” (3,3′-dimethyl-4-methoxybenzophenone),which is known as a safener for rice against damage by some herbicides,

“CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg.No. 54091-06-4), which is known as a safener against damage by someherbicides in rice.

S15) Compounds of the formula (S15) or tautomers thereof

as described in WO-A-2008/131861 and WO-A-2008/131860 in which

R_(H) ¹ is a (C₁-C₆)-haloalkyl radical and

R_(H) ² is hydrogen or halogen and

R_(H) ³, R_(H) ⁴ are independently hydrogen, (C₁-C₁₆)-alkyl,(C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl,

where each of the 3 latter radicals is unsubstituted or substituted byone or more radicals from the group of halogen, hydroxyl, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]amino, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl which is unsubstitutedor substituted, phenyl which is unsubstituted or substituted, andheterocyclyl which is unsubstituted or substituted,

or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl fused onone side of the ring to a 4 to 6-membered saturated or unsaturatedcarbocyclic ring, or (C₄-C₆)-cycloalkenyl fused on one side of the ringto a 4 to 6-membered saturated or unsaturated carbocyclic ring,

where each of the 4 latter radicals is unsubstituted or substituted byone or more radicals from the group consisting of halogen, hydroxyl,cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]amino, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl which is unsubstitutedor substituted, phenyl which is unsubstituted or substituted, andheterocyclyl which is unsubstituted or substituted,

or

R_(H) ³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or(C₂-C₄)-haloalkoxy and

R_(H) ⁴ is hydrogen or (C₁-C₄)-alkyl or

R_(H) ³ and R_(H) ⁴ together with the directly attached nitrogen atomrepresent a four- to eight-membered heterocyclic ring which, as well asthe nitrogen atom, may also contain further ring heteroatoms, preferablyup to two further ring heteroatoms from the group of N, O and S, andwhich is unsubstituted or substituted by one or more radicals from thegroup of halogen, cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio.

S16) Active compounds which are used primarily as herbicides but alsohave safener action on crop plants, for example

-   (2,4-dichlorophenoxy)acetic acid (2,4-D),-   (4-chlorophenoxy)acetic acid,-   (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),-   4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),-   (4-chloro-o-tolyloxy)acetic acid (MCPA),-   4-(4-chloro-o-tolyloxy)butyric acid,-   4-(4-chlorophenoxy)butyric acid,-   3,6-dichloro-2-methoxybenzoic acid (dicamba),-   1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate    (lactidichlor-ethyl).

Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide,isoxadifen-ethyl, cloquintocet-mexyl, dichlormid and metcamifen.

Wettable powders are preparations uniformly dispersible in water which,in addition to the active ingredient and apart from a diluent or inertsubstance, also comprise surfactants of ionic and/or nonionic type(wetting agent, dispersant), e.g. polyethoxylated alkylphenols,polyethoxylated fatty alcohols, polyethoxylated fatty amines, fattyalcohol polyglycolethersulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toproduce the wettable powders, the active herbicidal ingredients arefinely ground, for example in customary apparatuses such as hammermills, blower mills and air-jet mills, and simultaneously orsubsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the activeingredient in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which may be used are: calcium alkylarylsulfonate salts suchas calcium dodecylbenzenesulfonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide/ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dusting products are obtained by grinding the active ingredient withfinely distributed solids, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beproduced, for example, by wet-grinding by means of commercial bead millsand optional addition of surfactants as already listed above, forexample, for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be produced either by spraying the active ingredient ontogranular inert material capable of adsorption or by applying activeingredient concentrates to the surface of carrier substances, such assand, kaolinites or granular inert material, by means of adhesives, forexample polyvinyl alcohol, sodium polyacrylate or else mineral oils.Suitable active ingredients can also be granulated in the mannercustomary for the production of fertilizer granules—if desired as amixture with fertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized-bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London, J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations contain generally 0.1% to 99% by weight,especially 0.1% to 95% by weight, of compounds of the invention. Inwettable powders, the active ingredient concentration is, for example,about 10% to 90% by weight, the remainder to 100% by weight consistingof customary formulation constituents. In emulsifiable concentrates, theactive ingredient concentration may be about 1% to 90% and preferably 5%to 80% by weight. Formulations in the form of dusts comprise 1% to 30%by weight of active ingredient, preferably usually 5% to 20% by weightof active ingredient; sprayable solutions contain about 0.05% to 80% byweight, preferably 2% to 50% by weight of active ingredient. In the caseof water-dispersible granules, the active ingredient content dependspartially on whether the active ingredient is in liquid or solid formand on which granulation auxiliaries, fillers, etc., are used. In thewater-dispersible granules, the content of active ingredient is, forexample, between 1% and 95% by weight, preferably between 10% and 80% byweight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity.

On the basis of these formulations, it is also possible to producecombinations with other pesticidally active substances, for exampleinsecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

For application, the formulations in the commercial form are diluted ifappropriate in a customary manner, for example with water in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules. Preparations in dust form, granules for soilapplication or granules for scattering and sprayable solutions are notnormally diluted further with other inert substances prior toapplication.

The required application rate of the compounds of the formula (I) andtheir salts varies according to the external conditions such as, interalia, temperature, humidity and the type of herbicide used. It can varywithin wide limits, for example between 0.001 and 10.0 kg/ha or more ofactive substance, but it is preferably between 0.005 and 5 kg/ha, morepreferably in the range of from 0.01 to 1.5 kg/ha, more preferably inthe range of from 0.05 to 1 kg/ha. This applies both to pre-emergenceand to post-emergence application.

A carrier is a natural or synthetic, organic or inorganic substance withwhich the active ingredients are mixed or combined for betterapplicability, in particular for application to plants or plant parts orseed. The carrier, which may be solid or liquid, is generally inert andshould be suitable for use in agriculture.

Useful solid or liquid carriers include: for example ammonium salts andnatural rock dusts, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and synthetic rockdusts, such as finely divided silica, alumina and natural or syntheticsilicates, resins, waxes, solid fertilizers, water, alcohols, especiallybutanol, organic solvents, mineral and vegetable oils, and derivativesthereof. It is likewise possible to use mixtures of such carriers.Useful solid carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic meals, andalso granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks.

Suitable liquefied gaseous extenders or carriers are liquids which aregaseous at standard temperature and under atmospheric pressure, forexample aerosol propellants such as halogenated hydrocarbons, or elsebutane, propane, nitrogen and carbon dioxide.

In the formulations, it is possible to use tackifiers such ascarboxymethylcellulose, natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins, and synthetic phospholipids. Further additives may be mineraland vegetable oils.

When the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Useful liquid solventsare essentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or dichloromethane, aliphatichydrocarbons such as cyclohexane or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and alsowater.

The compositions of the invention may additionally comprise furthercomponents, for example surfactants. Useful surfactants are emulsifiersand/or foam formers, dispersants or wetting agents having ionic ornonionic properties, or mixtures of these surfactants. Examples thereofare salts of polyacrylic acid, salts of lignosulfonic acid, salts ofphenolsulfonic acid or naphthalenesulfonic acid, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (preferably alkylphenols or arylphenols),salts of sulfosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols,fatty acid esters of polyols, and derivatives of the compoundscontaining sulfates, sulfonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates,protein hydrolysates, lignosulfite waste liquors and methylcellulose.The presence of a surfactant is necessary if one of the activeingredients and/or one of the inert carriers is insoluble in water andwhen application is effected in water. The proportion of surfactants isbetween 5 and 40 percent by weight of the inventive composition. It ispossible to use dyes such as inorganic pigments, for example iron oxide,titanium oxide and Prussian Blue, and organic dyes such as alizarindyes, azo dyes and metal phthalocyanine dyes, and trace nutrients suchas salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

If appropriate, it is also possible for other additional components tobe present, for example protective colloids, binders, adhesives,thickeners, thixotropic substances, penetrants, stabilizers,sequestrants, complexing agents. In general, the active ingredients canbe combined with any solid or liquid additive commonly used forformulation purposes. In general, the compositions and formulations ofthe invention contain between 0.05% and 99% by weight, 0.01% and 98% byweight, preferably between 0.1% and 95% by weight, more preferablybetween 0.5% and 90% active ingredient, most preferably between 10 and70 percent by weight. The active ingredients or compositions of theinvention can be used as such or, depending on their respective physicaland/or chemical properties, in the form of their formulations or the useforms prepared therefrom, such as aerosols, capsule suspensions,cold-fogging concentrates, warm-fogging concentrates, encapsulatedgranules, fine granules, flowable concentrates for the treatment ofseed, ready-to-use solutions, dustable powders, emulsifiableconcentrates, oil-in-water emulsions, water-in-oil emulsions,macrogranules, microgranules, oil-dispersible powders, oil-miscibleflowable concentrates, oil-miscible liquids, foams, pastes, pesticidecoated seed, suspension concentrates, suspoemulsion concentrates,soluble concentrates, suspensions, sprayable powders, soluble powders,dusts and granules, water-soluble granules or tablets, water-solublepowders for the treatment of seed, wettable powders, natural productsand synthetic substances impregnated with active ingredient, and alsomicroencapsulations in polymeric substances and in coating materials forseed, and also ULV cold-fogging and warm-fogging formulations.

The formulations mentioned can be produced in a manner known per se, forexample by mixing the active ingredients with at least one customaryextender, solvent or diluent, emulsifier, dispersant and/or binder orfixative, wetting agent, water repellent, optionally siccatives and UVstabilizers and optionally dyes and pigments, antifoams, preservatives,secondary thickeners, tackifiers, gibberellins and other processingauxiliaries.

The compositions of the invention include not only formulations whichare already ready for use and can be deployed with a suitable apparatusonto the plant or the seed, but also commercial concentrates which haveto be diluted with water prior to use.

The active ingredients of the invention may be present as such or intheir (commercial standard) formulations, or else in the use formsprepared from these formulations as a mixture with other (known) activeingredients, such as insecticides, attractants, sterilants,bactericides, acaricides, nematicides, fungicides, growth regulators,herbicides, fertilizers, safeners or semiochemicals.

The inventive treatment of the plants and plant parts with the activeingredients or compositions is effected directly or by action on theirsurroundings, habitat or storage space by the customary treatmentmethods, for example by dipping, spraying, atomizing, irrigating,evaporating, dusting, fogging, broadcasting, foaming, painting,spreading-on, watering (drenching), drip irrigating and, in the case ofpropagation material, especially in the case of seeds, also by dry seedtreatment, wet seed treatment, slurry treatment, incrustation, coatingwith one or more coats, etc. It is also possible to deploy the activeingredients by the ultra-low volume method or to inject the activeingredient preparation or the active ingredient itself into the soil.

As also described below, the treatment of transgenic seed with theactive ingredients or compositions of the invention is of particularsignificance. This relates to the seed of plants containing at least oneheterologous gene which enables the expression of a polypeptide orprotein having insecticidal properties. The heterologous gene intransgenic seed can originate, for example, from microorganisms of thespecies Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. This heterologous gene preferablyoriginates from Bacillus sp., in which case the gene product iseffective against the European corn borer and/or the Western cornrootworm. The heterologous gene more preferably originates from Bacillusthuringiensis.

In the context of the present invention, the inventive composition isapplied to the seed alone or in a suitable formulation. Preferably, theseed is treated in a state in which it is sufficiently stable for nodamage to occur in the course of treatment. In general, the seed can betreated at any time between harvest and sowing. It is customary to useseed which has been separated from the plant and freed from cobs,shells, stalks, coats, hairs or the flesh of the fruits. For example, itis possible to use seed which has been harvested, cleaned and dried downto a moisture content of less than 15% by weight. Alternatively, it isalso possible to use seed which, after drying, for example, has beentreated with water and then dried again.

In general, when treating the seed, it has to be ensured that the amountof the composition of the invention and/or further additives applied tothe seed is chosen such that the germination of the seed is not impairedand the plant which arises therefrom is not damaged. This has to beensured particularly in the case of active ingredients which can exhibitphytotoxic effects at certain application rates.

The compositions of the invention can be applied directly, i.e. withoutcontaining any other components and without having been diluted. Ingeneral, it is preferable to apply the compositions to the seed in theform of a suitable formulation. Suitable formulations and methods forseed treatment are known to those skilled in the art and are described,for example, in the following documents: U.S. Pat. Nos. 4,272,417 A,4,245,432 A, 4,808,430, 5,876,739, US 2003/0176428 A1, WO 2002/080675A1, WO 2002/028186 A2.

The active ingredients of the invention can be converted to thecustomary seed-dressing formulations, such as solutions, emulsions,suspensions, powders, foams, slurries or other coating compositions forseed, and also ULV formulations.

These formulations are produced in a known manner, by mixing the activeingredients with customary additives, for example customary extendersand solvents or diluents, dyes, wetting agents, dispersants,emulsifiers, antifoams, preservatives, secondary thickeners, adhesives,gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofagrochemically active ingredients. Alkyl naphthalenesulfonates, such asdiisopropyl or diisobutyl naphthalenesulfonates, can be used withpreference.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of agrochemically active ingredients. Preference can begiven to using nonionic or anionic dispersants or mixtures of nonionicor anionic dispersants. Suitable nonionic dispersants include especiallyethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristryrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of agrochemically active ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substancesusable for such purposes in agrochemical compositions. Preferredexamples include cellulose derivatives, acrylic acid derivatives,xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The seed-dressing formulations usable in accordance with the inventioncan be used, either directly or after previously having been dilutedwith water, for the treatment of a wide range of different seed,including the seed of transgenic plants. In this case, additionalsynergistic effects may also occur in interaction with the substancesformed by expression.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention or with the preparations preparedtherefrom by addition of water, useful equipment is all mixing unitsusable customarily for seed dressing. Specifically, the seed dressingprocedure is to place the seed into a mixer, to add the particulardesired amount of seed-dressing formulations, either as such or afterprior dilution with water, and to mix them until the formulation isdistributed homogeneously on the seed. If appropriate, this is followedby a drying operation.

The active ingredients of the invention, given good plant compatibility,favourable homeotherm toxicity and good environmental compatibility, aresuitable for protection of plants and plant organs, for increasingharvest yields, and for improving the quality of the harvested crop.They can preferably be used as crop protection agents. They are activeagainst normally sensitive and resistant species and also against all orspecific stages of development.

Plants which can be treated in accordance with the invention include thefollowing main crop plants: maize, soya bean, cotton, Brassica oil seedssuch as Brassica napus (e.g. Canola), Brassica rapa, B. juncea (e.g.(field) mustard) and Brassica carinata, rice, wheat, sugar beet, sugarcane, oats, rye, barley, millet and sorghum, triticale, flax, grapes andvarious fruit and vegetables from various botanic taxa, for exampleRosaceae sp. (for example pome fruits such as apples and pears, but alsostone fruits such as apricots, cherries, almonds and peaches, and berryfruits such as strawberries), Ribesioidae sp., Juglandaceae sp.,Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceaesp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example bananatrees and plantations), Rubiaceae sp. (for example coffee), Theaceaesp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges andgrapefruit); Solanaceae sp. (for example tomatoes, potatoes, peppers,aubergines), Liliaceae sp., Compositae sp. (for example lettuce,artichokes and chicory—including root chicory, endive or commonchicory), Umbelliferae sp. (for example carrots, parsley, celery andceleriac), Cucurbitaceae sp. (for example cucumbers—including gherkins,pumpkins, watermelons, calabashes and melons), Alliaceae sp. (forexample leeks and onions), Cruciferae sp. (for example white cabbage,red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi,kohlrabi, radishes, horseradish, cress and chinese cabbage), Leguminosaesp. (for example peanuts, peas, and beans—for example common beans andbroad beans), Chenopodiaceae sp. (for example Swiss chard, fodder beet,spinach, beetroot), Malvaceae (for example okra), Asparagaceae (forexample asparagus); useful plants and ornamental plants in the gardenand woods; and in each case genetically modified types of these plants.

As mentioned above, it is possible to treat all plants and their partsin accordance with the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding techniques, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) which have been grown byconventional breeding, by mutagenesis or by recombinant DNA techniques.They may be cultivars, varieties, biotypes and genotypes.

The treatment method of the invention can be used for the treatment ofgenetically modified organisms (GMOs), e.g. plants or seeds. Geneticallymodified plants (or transgenic plants) are plants in which aheterologous gene has been stably integrated into the genome. The term“heterologous gene” means essentially a gene which is provided orassembled outside the plant and which, upon introduction into thenuclear genome, the chloroplast genome or the mitochondrial genome,imparts to the transformed plant novel or improved agronomical or othertraits because it expresses a protein or polypeptide of interest oranother gene which is present in the plant, or other genes which arepresent in the plant are down-regulated or switched off (for example bymeans of antisense technology, co-suppression technology or RNAitechnology [RNA interference]). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits specific presence in the plant genome is called a transformation ortransgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), theinventive treatment may also result in superadditive (“synergistic”)effects. For example, the following effects which exceed the effectsactually to be expected are possible: reduced application rates and/orwidened spectrum of activity and/or increased efficacy of the activeingredients and compositions which can be used in accordance with theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soilsalinity, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, greaterplant height, greener leaf colour, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products.

Plants and plant cultivars which are preferably treated in accordancewith the invention include all plants which have genetic material whichimparts particularly advantageous, useful traits to these plants(whether obtained by breeding and/or biotechnological means).

Examples of nematode-resistant plants are described, for example, in thefollowing U.S. patent application Ser. Nos. 11/765,491, 11/765,494,10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964,12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209,11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396and 12/497,221.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristics of heterosis, or hybrid effect,which results generally in higher yield, vigour, better health andresistance towards biotic and abiotic stress factors. Such plants aretypically produced by crossing an inbred male-sterile parent line (thefemale crossbreeding parent) with another inbred male-fertile parentline (the male crossbreeding parent). Hybrid seed is typically harvestedfrom the male-sterile plants and sold to growers. Male-sterile plantscan sometimes (e.g. in maize) be produced by detasselling (i.e. themechanical removal of the male reproductive organs or male flowers) but,more typically, male sterility is the result of genetic determinants inthe plant genome. In that case, and especially when seed is the desiredproduct to be harvested from the hybrid plants, it is typicallybeneficial to ensure that male fertility in hybrid plants, which containthe genetic determinants responsible for male sterility, is fullyrestored. This can be accomplished by ensuring that the malecrossbreeding parents have appropriate fertility restorer genes whichare capable of restoring the male fertility in hybrid plants thatcontain the genetic determinants responsible for male sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedfor Brassica species. However, genetic determinants for male sterilitycan also be located in the nuclear genome. Male-sterile plants can alsobe obtained by plant biotechnology methods such as genetic engineering.A particularly useful means of obtaining male-sterile plants isdescribed in WO 89/10396 in which, for example, a ribonuclease such as abarnase is selectively expressed in the tapetum cells in the stamens.Fertility can then be restored by expression in the tapetum cells of aribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate by various methods. Thus, forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., 1983,Science, 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genesencoding a petunia EPSPS (Shah et al., 1986, Science 233, 478-481), atomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or anEleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS.Glyphosate-tolerant plants can also be obtained by expressing a genethat encodes a glyphosate oxidoreductase enzyme. Glyphosate-tolerantplants can also be obtained by expressing a gene that encodes aglyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can alsobe obtained by selecting plants containing naturally-occurring mutationsof the abovementioned genes. Plants which express EPSPS genes whichimpart glyphosate tolerance have been described. Plants which expressother genes which impart glyphosate tolerance, for example decarboxylasegenes, have been described.

Other herbicide-resistant plants are for example plants made tolerant toherbicides inhibiting the enzyme glutamine synthase, such as bialaphos,phosphinothricin or glufosinate. Such plants can be obtained byexpressing an enzyme detoxifying the herbicide or a mutant of theglutamine synthase enzyme that is resistant to inhibition. One exampleof such an effective detoxifying enzyme is an enzyme encoding aphosphinothricin acetyltransferase (such as the bar or pat protein fromStreptomyces species). Plants expressing an exogenous phosphinothricinacetyltransferase have been described.

Further herbicide-tolerant plants are also plants that have been madetolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenases are enzymes thatcatalyse the reaction in which para-hydroxyphenylpyruvate (HPP) isconverted to homogentisate. Plants tolerant to HPPD inhibitors can betransformed with a gene encoding a naturally-occurring resistant HPPDenzyme, or a gene encoding a mutated or chimeric HPPD enzyme, asdescribed in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO2002/046387 or U.S. Pat. No. 6,768,044. Tolerance to HPPD inhibitors canalso be obtained by transforming plants with genes encoding certainenzymes enabling the formation of homogentisate despite inhibition ofthe native HPPD enzyme by the HPPD inhibitor. Such plants are describedin WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitorscan also be improved by transforming plants with a gene encoding aprephenate dehydrogenase enzyme in addition to a gene encoding anHPPD-tolerant enzyme, as described in WO 2004/024928. In addition,plants can be made more tolerant to HPPD inhibitors by inserting intothe genome thereof a gene which encodes an enzyme which metabolizes ordegrades HPPD inhibitors, for example CYP450 enzymes (see WO 2007/103567and WO 2008/150473).

Other herbicide-resistant plants are plants which have been renderedtolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. It is known that different mutations in the ALS enzyme (alsoknown as acetohydroxy acid synthase, AHAS) confer tolerance to differentherbicides and groups of herbicides, as described, for example, inTranel and Wright (Weed Science 2002, 50, 700-712). The production ofsulfonylurea-tolerant plants and imidazolinone-tolerant plants has beendescribed. Further sulfonylurea- and imidazolinone-tolerant plants havealso been described.

Further plants tolerant to imidazolinones and/or sulfonylureas can beobtained by induced mutagenesis, by selection in cell cultures in thepresence of the herbicide or by mutation breeding (cf., for example, forsoya beans U.S. Pat. No. 5,084,082, for rice WO 97/41218, for sugar beetU.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce U.S. Pat. No.5,198,599 or for sunflower WO 01/065922).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stress factors. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such stress resistance. Particularly usefulstress-tolerant plants include the following:

a. plants which contain a transgene capable of reducing the expressionand/or the activity of the poly(ADP-ribose) polymerase (PARP) gene inthe plant cells or plants;

b. plants which contain a stress tolerance-enhancing transgene capableof reducing the expression and/or the activity of the PARG-encodinggenes of the plants or plant cells;

c. plants which contain a stress tolerance-enhancing transgene codingfor a plant-functional enzyme of the nicotinamide adenine dinucleotidesalvage biosynthesis pathway, including nicotinamidase, nicotinatephosphoribosyltransferase, nicotinic acid mononucleotideadenyltransferase, nicotinamide adenine dinucleotide synthetase ornicotinamide phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage stability of theharvested product and/or altered properties of specific components ofthe harvested product such as, for example:

1) Transgenic plants which synthesize a modified starch which, in itsphysicochemical characteristics, in particular the amylose content orthe amylose/amylopectin ratio, the degree of branching, the averagechain length, the side chain distribution, the viscosity behaviour, thegelling strength, the starch granule size and/or the starch granulemorphology, is changed in comparison with the synthesized starch inwild-type plant cells or plants, so that this modified starch is bettersuited to specific applications.

2) Transgenic plants which synthesize non-starch carbohydrate polymersor which synthesize non-starch carbohydrate polymers with alteredproperties in comparison to wild-type plants without geneticmodification. Examples are plants which produce polyfructose, especiallyof the inulin and levan type, plants which produce alpha-1,4-glucans,plants which produce alpha-1,6-branched alpha-1,4-glucans, and plantsproducing alternan.

3) Transgenic plants which produce hyaluronan.

4) Transgenic plants or hybrid plants such as onions with particularproperties, such as “high soluble solids content”, “low pungency” (LP)and/or “long storage” (LS).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as cotton plants, with altered fibrecharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants containing a mutation imparting such alteredfibre characteristics and include:

a) plants, such as cotton plants, containing an altered form ofcellulose synthase genes;

b) plants, such as cotton plants, which contain an altered form of rsw2or rsw3 homologous nucleic acids, such as cotton plants with anincreased expression of sucrose phosphate synthase;

c) plants, such as cotton plants, with increased expression of sucrosesynthase;

d) plants, such as cotton plants, wherein the timing of theplasmodesmatal gating at the basis of the fibre cell is altered, forexample through downregulation of fibre-selective 0-1,3-glucanase;

e) plants, such as cotton plants, which have fibres with alteredreactivity, for example through expression of theN-acetylglucosaminetransferase gene, including nodC, and chitin synthasegenes.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered oil profile characteristics. Such plants can be obtained bygenetic transformation, or by selection of plants containing a mutationimparting such altered oil characteristics and include:

a) plants, such as oilseed rape plants, which produce oil having a higholeic acid content;

b) plants, such as oilseed rape plants, which produce oil having a lowlinolenic acid content;

c) plants, such as oilseed rape plants, which produce oil having a lowlevel of saturated fatty acids.

Plants or plant cultivars (which can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants such as potatoes which are virus-resistant,for example to the potato virus Y (SY230 and SY233 events fromTecnoplant, Argentina), or which are resistant to diseases such aspotato late blight (e.g. RB gene), or which exhibit reduced cold-inducedsweetness (which bear the genes Nt-Inh, II-INV) or which exhibit thedwarf phenotype (A-20 oxidase gene).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered seed shattering characteristics. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such altered characteristics, and include plantssuch as oilseed rape with retarded or reduced seed shattering.

Particularly useful transgenic plants which can be treated according tothe invention are plants with transformation events or combinations oftransformation events which are the subject of granted or pendingpetitions for nonregulated status in the USA at the Animal and PlantHealth Inspection Service (APHIS) of the United States Department ofAgriculture (USDA). Information relating to this is available at anytime from APHIS (4700 River Road Riverdale, Md. 20737, USA), for examplevia the website http://www.aphis.usda.gov/brs/not_reg.html. At thefiling date of this application, the petitions with the followinginformation were either granted or pending at APHIS:

-   -   Petition: Identification number of the petition. The technical        description of the transformation event can be found in the        specific petition document available from APHIS on the website        via the petition number. These descriptions are hereby disclosed        by reference.    -   Extension of a petition: Reference to an earlier petition for        which an extension of scope or term is being requested.    -   Institution: Name of the person submitting the petition.    -   Regulated article: The plant species in question.    -   Transgenic phenotype: The trait imparted to the plant by the        transformation event.    -   Transformation event or line: The name of the event(s)        (sometimes also referred to as line(s)) for which nonregulated        status is being requested.    -   APHIS documents: Various documents which have been published by        APHIS with regard to the petition or can be obtained from APHIS        on request.

Particularly useful transgenic plants which can be treated in accordancewith the invention are plants which comprise one or more genes whichcode for one or more toxins, for example the transgenic plants which aresold under the following trade names: YIELD GARD® (for example maize,cotton, soya beans), KnockOut® (for example maize), BiteGard® (forexample maize), BT-Xtra® (for example maize), StarLink® (for examplemaize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton),NatureGard® (for example maize), Protecta® and NewLeaf® (potato).Examples of herbicide-tolerant plants which may be mentioned includemaize varieties, cotton varieties and soya bean varieties which areavailable under the following trade names: Roundup Ready® (tolerance toglyphosates, for example maize, cotton, soya beans), Liberty Link®(tolerance to phosphinothricin, for example oilseed rape), IMI®(tolerance to imidazolinone) and SCS® (tolerance to sulfonylurea), forexample maize. Herbicide-resistant plants (plants bred in a conventionalmanner for herbicide tolerance) which may be mentioned include thevarieties sold under the name Clearfield® (for example maize).

The examples which follow illustrate the present invention.

EXAMPLES

The present invention is illustrated in detail by the examples whichfollow, but these examples do not restrict the invention in any way.

A. Synthesis Examples

Methyl(2R)-2-{[4-bromo-1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-yl]oxy}propanoate(1-182): To a solution of 0.40 g (1.01 mmol) of methyl(2R)-2-{[1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-yl]oxy}propanoatein 14 ml of DMF was added 0.22 g (1.22 mmol) of N-bromosuccinimide, andthe mixture was stirred at 65° C. for one hour. The solvent was removedunder reduced pressure, the residue was taken up in water and extractedrepeatedly with methylene chloride, the combined organic phases weredried over sodium sulfate, and the solvent was removed under reducedpressure. After purification by column chromatography on silica gel witha heptane/ethyl acetate gradient (start with heptane/ethyl acetate=95:5,to heptane/ethyl acetate=50:50 within 20 min), 0.36 g (71%) of a productwith m/z (%)=473 (50) [M⁺], 475 (50) [M⁺] and a specific angle ofrotation of [α]=+20° was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.57 (d,3H), 3.69 (s, 3H), 5.15 (q, 1H), 7.18 (m, 1H), 7.36 (m, 2H), 7.50 (m,3H).

Synthesis of the Starting Compounds:

Methyl(2R)-2-{[1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-yl]oxy}propanoate:To a solution of 0.50 g (1.54 mmol) of1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-ol in 31 g ofdimethylformamide was added 0.75 g (2.31 mmol) of caesium carbonate, themixture was stirred at room temperature for 10 minutes, 0.23 g (1.85mmol) of methyl (2S)-2-chloropropanoate was added, and the mixture wasstirred at 80° C. for a further hour. The solvent was removed underreduced pressure, the residue was taken up in water and extractedrepeatedly with methylene chloride, the combined organic phases weredried over sodium sulfate, and the solvent was removed under reducedpressure. After purification by column chromatography on silica gel withheptane/ethyl acetate (start with heptane/ethyl acetate=95:5, toheptane/ethyl acetate=50:50 within 12 min), 0.46 g (72%) of a productwith m/z=395 [M⁺] and a specific angle of rotation of [α]=+40° wasobtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.63 (d, 3H), 3.78 (s, 3H), 5.18(q, 1H), 6.03 (s, 1H), 6.91 (m, 1H), 7.08 (m, 4H), 7.16 (m, 1H).

-   b) 1-(2,5-Difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-ol: To    a solution of 4.95 g (9.64 mmol) of    N′-(2,5-difluorophenyl)-3-(3,4-difluorophenyl)prop-2-yne hydrazide    in 10 ml of DMF was added 0.15 g (0.77 mmol) of copper(I) iodide,    and the mixture was stirred at 80° C. for one hour. After    purification by column chromatography on silica gel with    heptane/ethyl acetate (start with heptane/ethyl acetate=95:5, to    heptane/ethyl acetate=20:80 within 15 min), 1.06 g (28%) of a    product with m/z=309 [M⁺] was obtained. ¹H-NMR (400 MHz, d₆-DMSO):    δ=6.09 (s, 1H), 7.02 (m, 1H), 7.40 (m, 4H), 7.50 (m, 1H), 10.41 (s,    1H).-   c) N′-(2,5-Difluorophenyl)-3-(3,4-difluorophenyl)prop-2-yne    hydrazide: To a solution of 2.14 g (11.75 mmol) of    3-(3,4-difluorophenyl)prop-2-ynoic acid in 20 ml of tetrahydrofuran    were successively added 1.86 g (12.92 mmol) of    (2,5-difluorophenyl)hydrazine and 5.94 g (58.75 mmol) of    triethylamine. 11.22 g (17.62 mmol) of propanephosphonic anhydride    (T3P, 50% solution in tetrahydrofuran) was added dropwise, and the    mixture was stirred at room temperature for one hour. The reaction    mixture was poured onto water and extracted repeatedly with methyl    acetate, the combined organic phases were dried over magnesium    sulfate, the solvent was removed under reduced pressure, and 4.97 g    (80%) of an oily product (HPLC/MS purity=80%, m/z=309 [M⁺]), which    was converted further without purification.-   d) 3-(3,4-Difluorophenyl)prop-2-ynoic acid: Under an argon    atmosphere, the following were added successively to 5.00 g (20.83    mmol) of 1,2-difluoro-4-iodobenzene in 30 ml of dry tetrahydrofuran:    1.46 g (20.83 mmol) of propiolic acid, 0.29 g (0.42 mmol) of    bis(triphenylphosphine)palladium(11) dichloride, 0.16 g (0.83 mmol)    of copper(I)iodide and 7.38 g (72.92 mmol) of diisopropylamine. The    mixture was stirred at room temperature for 2 hours, the reaction    mixture was added to water, 15.00 ml of 2 N hydrochloric acid was    added and extraction was effected repeatedly with ethyl acetate. The    combined organic phases were dried over sodium sulfate and    concentrated under reduced pressure. After purification by column    chromatography on silica gel with heptane/ethyl acetate (start with    heptane/ethyl acetate=95:5, to heptane/ethyl acetate=40:60 within 15    min), 2.89 g (76%) of a product with m/z=183 [M⁺] was obtained.    ¹H-NMR (400 MHz, d₆-DMSO): δ=7.56 (m, 2H), 7.86 (m, 1H), 13.95 (bs,    1H).

Methyl(2R)-2-{[4-cyano-1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-yl]oxy}propanoate(I-185): A mixture consisting of 0.18 g (0.37 mmol) of methyl(2R)-2-{[4-bromo-1-(2,5-difluorophenyl)-5-(3,4-difluorophenyl)-1H-pyrazol-3-yl]oxy}propanoate(I-182), 0.04 g (0.35 mmol) of zinc cyanide and 0.04 g (0.04 mmol) oftetrakis(triphenylphosphine)palladium in 5 ml of dimethylacetamide washeated to 180° C. in a microwave under an argon atmosphere for 40minutes. The solvent was removed under reduced pressure, the residue wastaken up in water/methylene chloride, the aqueous phase was extractedrepeatedly with methylene chloride, the combined organic phases weredried over sodium sulfate, and the solvent was removed under reducedpressure. After purification by column chromatography on silica gel witha heptane/ethyl acetate gradient (start with heptane/ethyl acetate=95:5,to heptane/ethyl acetate=60:40 within 15 min), 0.11 g (67%) of a productwith m/z=420 [M⁺] and a specific angle of rotation of [α]=+170 wasobtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.68 (d, 3H), 3.78 (s, 3H), 5.18(q, 1H), 7.12 (m, 6H).

Methyl2-{[4-chloro-5-(3,5-difluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoate(I-165): A reaction mixture consisting of 150.0 mg (0.35 mmol) of methyl2-[(4-chloro-5-iodo-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate, 83.0 mg(0.53 mmol) of (3,5-difluorophenyl)boronic acid, 12.3 mg (0.02 mmol) ofbis(triphenylphosphine)palladium(II) dichloride, 228.4 mg (0.70 mmol) ofcaesium carbonate (2.5 molar aqueous solution) and 4.4 ml of1,2-dimethoxyethane was heated to 80° C. for 3 hours. The solvent wasremoved under reduced pressure, the residue was taken up in water/ethylacetate, the aqueous phase was extracted repeatedly with ethyl acetate,the combined organic phases were dried over sodium sulfate, and thesolvent was removed under reduced pressure. After purification by columnchromatography on silica gel with heptane/ethyl acetate, 0.11 g (67%) ofa product with m/z (%)=393 (76) [M⁺], 395 (24) [M⁺] was obtained. ¹H-NMR(400 MHz, CDCl₃): δ=1.69 (d, 3H), 3.79 (s, 3H), 5.24 (q, 1H), 6.82 (m,3H), 7.12 (m, 2H), 7.29 (m, 3H).

Synthesis of the Starting Compounds:

-   a) Methyl    2-[(4-chloro-5-iodo-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate: To a    solution of 2.80 g (9.47 mmol) of methyl    2-[(5-amino-4-chloro-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate in 56    ml of acetonitrile were successively added 10.14 g (37.87 mmol) of    diiodomethane and 2.22 g (18.94 mmol) of isopentyl nitrite, and the    mixture was heated to 50° C. for 30 minutes. The solvent was removed    under reduced pressure, the residue was taken up in water/ethyl    acetate, the aqueous phase was extracted repeatedly with ethyl    acetate, the combined organic phases were dried over sodium sulfate,    and the solvent was removed under reduced pressure. After    purification by column chromatography on silica gel with    heptane/ethyl acetate, 2.59 g (64%) of a yellowish solid with m/z    (%)=407 (76) [M⁺], 409 (24) [M⁺] was obtained. ¹H-NMR (400 MHz,    CDCl₃): δ=1.65 (d, 3H), 3.75 (s, 3H), 5.17 (q, 1H), 7.41 (m, 2H),    7.45 (m, 3H).-   b) Methyl    2-[(5-amino-4-chloro-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate: To a    solution of 0.80 g (2.76 mmol) of methyl    2-[(5-amino-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate in 5.0 ml of    dimethylformamide was added 0.44 g (3.31 mmol) of    N-chlorosuccinimide, and the mixture was stirred at room temperature    for 30 minutes. The solvent was removed under reduced pressure, the    residue was taken up in water/methylene chloride, the aqueous phase    was extracted repeatedly with methylene chloride, the combined    organic phases were dried over sodium sulfate, and the solvent was    removed under reduced pressure. After purification by column    chromatography on silica gel with heptane/ethyl acetate, 0.50 g    (59%) of a colourless solid with m/z (%)=296 (76) [M⁺], 298 (24)    [M⁺] was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.64 (d, 3H), 3.76 (s,    3H), 3.91 (bs, 2H), 5.20 (q, 1H), 7.30 (m, 1H), 7.45 (m, 4H).-   c) Methyl 2-[(5-amino-1-phenyl-1H-pyrazol-3-yl)oxy]propanoate: To a    solution of 0.20 g (1.09 mmol) of 5-amino-1-phenyl-1H-pyrazol-3-ol    in 5.0 ml of dimethylformamide was added 0.53 g (1.63 mmol) of    caesium carbonate, the mixture was stirred at room temperature for    10 minutes, 0.22 g (1.30 mmol) of methyl 2-bromopropanoate was    added, and the mixture was stirred at room temperature for 2 hours.    The mixture was filtered, the filtrate was concentrated under    reduced pressure, and the residue was stirred with dimethyl ether.    This gave 0.19 g (64%) of a crystalline product with m/z=262 [M⁺].    ¹H-NMR (400 MHz, CDCl₃): δ=1.59 (d, 3H), 3.77 (s, 3H), 3.80 (bs,    2H), 5.16 (q, 1H), 5.20 (s, 1H), 7.26 (m, 1H), 7.45 (m, 2H), 7.49    (m, 2H).

Methyl{[4-chloro-1-(2-fluorophenyl)-5-(5-fluoro-2-thienyl)-1H-pyrazol-3-yl]oxy}acetate(1-094): To a solution of 85.0 mg (0.24 mmol) of methyl{[1-(2-fluorophenyl)-5-(5-fluoro-2-thienyl)-1H-pyrazol-3-yl]oxy}acetatein 3.2 ml of dimethylformamide was added 42.0 mg (0.32 mmol) ofN-chlorosuccinimide in portions, and the mixture was stirred at roomtemperature for 14 hours. The solvent was removed under reducedpressure, the residue was taken up in water/methylene chloride, theorganic phase was washed with saturated aqueous sodium hydrogencarbonatesolution and water, the combined aqueous phases were extractedrepeatedly with methylene chloride, the combined organic phases weredried over sodium sulfate, and the solvent was removed under reducedpressure. This gave 78 g (67%) of a product with m/z (%)=385 (76) [M⁺],387 (24) [M⁺]. ¹H-NMR (400 MHz, CDCl₃): δ=3.79 (s, 3H), 4.90 (s, 2H),6.38 (d, 2H), 6.72 (d, 2H), 7.16 (t, 1H), 7.24 (m, 1H), 7.41 (m, 2H).

Synthesis of the Starting Compounds:

-   a) Methyl    {[1-(2-fluorophenyl)-5-(5-fluoro-2-thienyl)-1H-pyrazol-3-yl]oxy}acetate:    Under an argon atmosphere, the following were added successively to    a solution of 0.40 g (1.06 mmol) of methyl    {[1-(2-fluorophenyl)-5-iodo-1H-pyrazol-3-yl]oxy}acetate in 6.1 ml of    dioxane: 37.0 mg (0.05 mmol) of bis(triphenylphosphine)palladium(II)    dichloride, 0.24 g (1.06 mmol) of    2-(5-fluoro-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.44    g (3.19 mmol) of potassium carbonate, 0.4 ml of water, and the    mixture was heated under reflux for 6 hours. The solvent was removed    under reduced pressure, the residue was taken up in water/methylene    chloride, the aqueous phase was extracted repeatedly with methylene    chloride, the combined organic phases were dried over sodium    sulfate, and the solvent was removed under reduced pressure. After    purification by column chromatography on silica gel with    heptane/ethyl acetate, 0.18 g (38%) of a product with m/z (%)=351    [M⁺] was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=3.80 (s, 3H), 4.84 (s,    2H), 6.06 (s, 1H), 6.31 (d, 2H), 6.45 (d, 2H), 7.18 (t, 1H), 7.28    (m, 1H), 7.44 (m, 2H).-   b) Methyl {[1-(2-fluorophenyl)-5-iodo-1H-pyrazol-3-yl]oxy}acetate To    a solution of 2.69 g (8.85 mmol) of    1-(2-fluorophenyl)-5-iodo-1H-pyrazol-3-ol in 197 ml of acetonitrile    was added 3.67 g (26.54 mmol) of potassium carbonate, the mixture    was stirred at room temperature for 10 minutes, 1.35 g (8.85 mmol)    of methyl bromoacetate was added, and the mixture was stirred under    reflux for 8 hours. The mixture was filtered, the filtrate was    concentrated under reduced pressure, the residue was taken up in    water/methylene chloride, the aqueous phase was extracted repeatedly    with methylene chloride, the combined organic phases were dried over    sodium sulfate, and the solvent was removed under reduced pressure.    After purification by column chromatography on silica gel with    heptane/ethyl acetate, 1.81 g (54%) of a product with m/z (%)=377    [M⁺] was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=3.78 (s, 3H), 4.80 (s,    2H), 6.18 (s, 1H), 7.22 (m, 2H), 7.39 (m, 1H), 7.45 (m, 1H).-   c) 1-(2-Fluorophenyl)-5-iodo-1H-pyrazol-3-ol: To a solution of 4.70    g (11.24 mmol) of    3-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-fluorophenyl)-5-iodo-1H-pyrazole    in 105 ml of tetrahydrofuran was added 3.82 g (14.61 mmol) of    tetra-n-butylammonium fluoride, and the mixture was stirred at room    temperature for 4 hours. The solvent was removed under reduced    pressure, the residue was taken up in water/ethyl acetate, the    aqueous phase was extracted repeatedly with ethyl acetate, the    combined organic phases were dried over sodium sulfate, and the    solvent was removed under reduced pressure. After purification by    column chromatography on silica gel with heptane/ethyl acetate, 2.37    g (69%) of a product with m/z (%)=305 [M⁺] was obtained. ¹H-NMR (400    MHz, CDCl₃): δ=6.01 (s, 1H), 7.30 (m, 2H), 7.42 (m, 1H), 7.48 (m,    1H), 10.56 (bs, 1H).-   d)    3-{[tert-Butyl(dimethyl)silyl]oxy}-1-(2-fluorophenyl)-5-iodo-1H-pyrazole:    Under argon, a solution of 6.00 g (20.52 mmol) of    3-{[tert-butyl(dimethyl)silyl]oxy}-1-(2-fluorophenyl)-1H-pyrazole in    98 ml of tetrahydrofuran was added to a mixture of 1.71 g (26.67    mmol) of n-butyllithium and 2.70 g (26.67 mmol) of diisopropylamine    in 98 ml of tetrahydrofuran, and the mixture was stirred at −78° C.    for one hour. A solution of 6.77 g (26.67 mmol) of iodine in 98 ml    of tetrahydrofuran was added dropwise, and the mixture was stirred    at −78° C. for a further hour. The mixture was allowed to warm up to    room temperature, water was added, and extraction was effected    repeatedly with ethyl acetate. The combined organic phases were    dried over sodium sulfate, and the solvent was removed under reduced    pressure. After purification by column chromatography on silica gel    with heptane/ethyl acetate, 4.72 g (55%) of a product with m/z    (%)=419 [M⁺] was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=0.26 (s, 6H),    0.98 (s, 9H), 6.02 (s, 1H), 7.23 (m, 2H), 7.40 (m, 2H).-   e)    3-{[tert-Butyl(dimethyl)silyl]oxy}-1-(2-fluorophenyl)-1H-pyrazole:    To a solution of 20.00 g (112.26 mmol) of    1-(2-fluorophenyl)-1H-pyrazol-3-ol in 900 ml of dichloromethane were    successively added 21.05 g (208.1 mmol) of triethylamine and 15.32 g    (101.64 mmol) of tert-butyl(chloro)dimethylsilane, and the mixture    was stirred at room temperature for 4 hours. The solvent was removed    under reduced pressure, and 29.60 g (quant.) of a product with    m/z=293 [M⁺] was obtained, which was converted further without    purification. ¹H-NMR (400 MHz, CDCl₃): δ=0.31 (s, 6H), 1.00 (s, 9H),    5.85 (d, 1H), 7.17 (m, 3H), 7.84 (m, 2H).

Methyl2-{[4-bromo-5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoate(I-132): To a solution of 1.10 g (2.91 mmol) of methyl2-{[5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoate in 16 mlof DMF was added 0.57 g (3.20 mmol) of N-bromosuccinimide, and themixture was stirred at 70° C. for three hours. The solvent was removedunder reduced pressure, the residue was taken up in water and extractedrepeatedly with methylene chloride, the combined organic phases weredried over sodium sulfate, and the solvent was removed under reducedpressure. After purification by column chromatography on silica gel withheptane/ethyl acetate, 1.04 g (81%) of a product with m/z (%)=419 (50)[M⁺], 421 (50) [M⁺] was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.69 (d,3H), 3.79 (s, 3H), 5.26 (q, 1H), 7.07 (m, 4H), 7.22 (m, 5H).

Synthesis of the starting compounds: The starting compounds weresynthesized by the methods described in Example No. I-182.

2-{[4-Bromo-5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoicacid (I-138)

A mixture of 1.00 g (2.27 mmol) of methyl2-{[4-bromo-5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoate(I-132), 0.73 g (18.25 mmol) of 2N sodium hydroxide solution and 5 ml oftetrahydrofuran was stirred at room temperature for three hours. Thesolvent was removed under reduced pressure, and the remaining organicphase was adjusted to pH 2 with 2 N HCl. The precipitated solids weredried at 40° C. under reduced pressure, and 0.90 g (93%) of a colourlesssolid with m/z (%)=405 (50) [M⁺], 407 (50) [M⁺] was obtained. ¹H-NMR(400 MHz, CDCl₃): δ=1.71 (d, 3H), 5.27 (q, 1H), 7.08 (m, 4H), 7.25 (m,5H).

MethylN-(2-{[4-bromo-5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoyl)glycinate(III-056)

Under argon, the following were added successively to a solution of 0.15g (0.35 mmol) of2-{[4-bromo-5-(4-fluorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}propanoicacid (I-138) in 4 ml of tetrahydrofuran: 2.13 g (1.68 mmol) of2-methoxy-2-oxoethanaminium chloride, 1.71 g (1.68 mmol) ofpropanephosphonic anhydride (T3P, 50% solution in tetrahydrofuran) and0.34 g (3.36 mmol) of triethylamine, and the mixture was stirred at 50°C. for 6 hours. The solvent was removed under reduced pressure, theresidue was taken up in water and extracted repeatedly with methylenechloride, the combined organic phases were dried over sodium sulfate,and the solvent was removed under reduced pressure. After purificationby column chromatography on silica gel with heptane/ethyl acetate, 0.14g (79%) of a colourless oil with m/z (%)=478 (50) [M⁺], 476 (50) [M⁺]was obtained. ¹H-NMR (400 MHz, CDCl₃): δ=1.71 (d, 3H), 3.77 (s, 3H),4.12 (m, 2H), 5.35 (q, 1H), 7.08 (m, 2H), 7.15 (m, 3H), 7.26 (m, 5H).

NMR data of selected examples:

The ¹H NMR data of selected examples of compounds of the general formula(I) are stated in two different ways, namely (a) conventional NMRevaluation and interpretation or (b) in the form of ¹H NMR peak listsaccording to the method described further down.

a) Conventional NMR Interpretation

I-094: ¹H-NMR (400 MHz, CDCl₃): δ=3.79 (s, 3H), 4.90 (s, 2H), 6.38 (d,2H), 6.72 (d, 2H), 7.16 (t, 1H), 7.24 (m, 1H), 7.41 (m, 2H).

I-125: ¹H-NMR (400 MHz, CDCl₃): δ=1.70 (d, 3H), 3.79 (s, 3H), 5.23 (q,1H), 6.88 (m, 1H), 7.0 (m, 3H), 7.17 (m, 2H), 7.27 (m, 1H), 7.40 (m,1H).

I-132: ¹H-NMR (400 MHz, CDCl₃): δ=1.69 (d, 3H), 3.79 (s, 3H), 5.26 (q,1H), 7.07 (m, 4H), 7.22 (m, 5H).

I-138: ¹H-NMR (400 MHz, CDCl₃): δ=1.71 (d, 3H), 5.27 (q, 1H), 7.08 (m,4H), 7.25 (m, 5H).

I-143: ¹H-NMR (400 MHz, CDCl₃): δ=1.28 (t, 3H), 4.27 (q, 2H), 4.98 (s,2H), 7.11 (m, 5H), 7.33 (t, 1H), 7.40 (m, 1H).

I-145: ¹H-NMR (400 MHz, CDCl₃): δ=1.69 (d, 3H), 3.79 (s, 3H), 5.26 (q,1H), 7.08 (m, 4H), 7.25 (m, 5H).

I-165: ¹H-NMR (400 MHz, CDCl₃): δ=1.69 (d, 3H), 3.79 (s, 3H), 5.24 (q,1H), 6.82 (m, 3H), 7.12 (m, 2H), 7.29 (m, 3H).

I-181: ¹H-NMR (400 MHz, CDCl₃): δ=3.81 (s, 3H), 4.91 (s, 2H), 7.00 (m,3H), 7.13 (m, 3H).

I-182: ¹H-NMR (400 MHz, CDCl₃): δ=1.57 (d, 3H), 3.69 (s, 3H), 5.15 (q,1H), 7.18 (m, 1H), 7.36 (m, 2H), 7.50 (m, 3H).

I-183: ¹H-NMR (400 MHz, CDCl₃): δ=3.81 (s, 3H), 4.91 (s, 2H), 7.07 (m,1H), 7.13 (m, 3H), 7.21 (m, 2H).

I-184: ¹H-NMR (400 MHz, CDCl₃): δ=1.67 (d, 3H), 3.77 (s, 3H), 5.22 (q,1H), 6.98 (m, 1H), 7.02 (m, 1H), 7.12 (m, 2H), 7.17 (t, 1H), 7.32 (m,2H).

I-185: ¹H-NMR (400 MHz, CDCl₃): δ=1.68 (d, 3H), 3.78 (s, 3H), 5.18 (q,1H), 7.12 (m, 6H).

III-056: ¹H-NMR (400 MHz, CDCl₃): δ=1.71 (d, 3H), 3.77 (s, 3H), 4.12 (m,2H), 5.35 (q, 1H), 7.08 (m, 2H), 7.15 (m, 3H), 7.26 (m, 5H).

b) NMR Peak List Method

The ¹H NMR data of selected examples may also be stated in the form of¹H NMR peak lists. For each signal peak, first the δ value in ppm andthen the signal intensity in round brackets are listed. The δvalue—signal intensity number pairs for different signal peaks arelisted with separation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . α_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

To calibrate the chemical shift of ¹H-NMR spectra, we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which arelikewise provided by the invention, and/or peaks of impurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of ¹H NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of ¹H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

I-022: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4060 (1.0); 7.4002 (1.6); 7.3929(0.8); 7.3856 (1.8); 7.3822 (2.4); 7.3778 (1.4); 7.3706 (0.8); 7.3639(2.0); 7.3608 (0.9); 7.3585 (0.8); 7.3502 (0.9); 7.3458 (3.0); 7.3283(1.7); 7.3250 (1.2); 7.3188 (0.5); 7.3139 (2.6); 7.3116 (2.2); 7.3100(2.3); 7.2988 (0.5); 7.2936 (1.4); 7.2889 (1.1); 7.2593 (32.9); 7.2236(0.7); 7.2063 (0.9); 7.2039 (1.2); 7.0878 (0.7); 7.0850 (0.6); 7.0662(0.7); 7.0628 (1.2); 7.0602 (0.8); 7.0415 (0.6); 7.0378 (0.6); 4.9164(9.0); 3.8062 (16.0); 1.5424 (0.8); −0.0002 (12.9) I-054: ¹H-NMR(400.0MHz, CDCl3): δ = 7.3511 (0.6); 7.3467 (0.7); 7.3322 (1.4); 7.3244 (2.8);7.3202 (2.8); 7.3139 (1.8); 7.3111 (1.5); 7.3064 (2.5); 7.3039 (2.4);7.2988 (0.8); 7.2970 (1.0); 7.2940 (1.4); 7.2922 (1.0); 7.2845 (1.2);7.2834 (1.2); 7.2793 (3.1); 7.2745 (2.3); 7.2702 (0.9); 7.2685 (1.0);7.2637 (1.2); 7.2622 (1.3); 7.2582 (19.1); 7.2546 (1.2); 7.1584 (0.6);7.1566 (0.6); 7.1550 (0.7); 7.1535 (0.6); 7.1356 (0.9); 7.0253 (0.7);7.0220 (0.6); 7.0045 (0.6); 7.0006 (1.1); 6.9969 (0.7); 6.9795 (0.6);6.9762 (0.5); 5.2961 (1.8); 4.9226 (8.9); 3.8029 (16.0); −0.0002 (7.2)I-055: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3769 (0.6); 7.3623 (1.1); 7.3578(1.4); 7.3433 (1.0); 7.3391 (1.2); 7.3310 (0.7); 7.3229 (0.5); 7.3107(0.5); 7.2597 (20.0); 7.2089 (0.6); 7.2073 (0.7); 7.2056 (0.7); 7.1896(0.9); 7.1879 (1.0); 7.1862 (1.0); 7.1487 (0.6); 7.1434 (0.6); 7.1390(0.6); 7.1300 (0.6); 7.1246 (0.7); 7.1216 (0.7); 7.1172 (1.2); 7.1142(0.7); 7.1029 (0.6); 7.0976 (1.3); 7.0929 (0.9); 7.0725 (0.7); 7.0558(0.7); 7.0525 (0.6); 7.0351 (0.6); 7.0311 (1.0); 7.0274 (0.6); 7.0099(1.0); 7.0064 (1.0); 6.9993 (0.6); 6.9956 (0.7); 5.2980 (4.1); 4.9117(9.0); 3.8010 (16.0); 2.9549 (0.6); 2.8837 (0.5); 2.8825 (0.5); 1.5420(2.6); −0.0002 (7.6) I-056: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.2897 (0.6);7.2878 (0.8); 7.2826 (3.3); 7.2785 (1.1); 7.2770 (1.3); 7.2737 (0.9);7.2689 (3.9); 7.2680 (4.0); 7.2662 (4.6); 7.2593 (62.1); 7.2518 (2.2);7.2474 (6.0); 7.2386 (1.2); 7.2345 (2.3); 7.2307 (1.4); 7.2237 (0.6);7.2174 (1.5); 7.1987 (0.5); 7.1342 (1.6); 7.1324 (2.9); 7.1285 (4.0);7.1228 (1.0); 7.1156 (1.6); 7.1131 (1.2); 7.1112 (2.8); 7.1080 (2.2);7.0752 (3.1); 7.0696 (0.9); 7.0609 (0.5); 7.0582 (1.0); 7.0536 (4.5);7.0483 (0.9); 7.0369 (0.8); 7.0315 (2.4); 4.9188 (13.3); 4.3060 (1.7);4.2881 (5.4); 4.2703 (5.5); 4.2525 (1.8); 4.2304 (0.5); 1.5403 (16.0);1.3199 (7.1); 1.3021 (14.6); 1.2925 (0.8); 1.2842 (7.0); 0.0080 (0.6);−0.0002 (22.6); −0.0085 (0.6) I-057: ¹H-NMR(400.0 MHz, CDCl3): δ =7.5182 (1.7); 7.3087 (1.0); 7.3026 (0.8); 7.2985 (1.0); 7.2970 (1.1);7.2929 (0.8); 7.2882 (1.3); 7.2857 (3.0); 7.2808 (4.1); 7.2771 (2.0);7.2724 (3.7); 7.2691 (3.1); 7.2660 (4.4); 7.2593 (288.4); 7.2536 (6.4);7.2500 (4.5); 7.2456 (0.8); 7.2431 (1.4); 7.2370 (1.3); 7.2354 (1.3);7.2265 (0.6); 7.1557 (0.6); 7.1515 (0.8); 7.1452 (2.8); 7.1410 (3.4);7.1351 (1.3); 7.1311 (0.7); 7.1287 (1.4); 7.1241 (2.8); 7.1207 (2.3);7.0826 (3.2); 7.0770 (1.0); 7.0683 (0.6); 7.0657 (1.0); 7.0612 (4.9);7.0558 (1.0); 7.0443 (0.8); 7.0390 (2.5); 6.9953 (1.7); 4.9952 (16.0);0.3308 (0.6); 0.2375 (0.6); 0.0079 (3.5); −0.0002 (130.0); −0.0085 (3.9)I-058: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3327 (0.7); 7.3289 (1.8); 7.3248(1.5); 7.3208 (5.1); 7.3166 (5.2); 7.3101 (3.8); 7.3056 (3.4); 7.3028(4.2); 7.3006 (3.6); 7.2942 (1.7); 7.2903 (2.2); 7.2868 (2.1); 7.2838(1.2); 7.2818 (1.3); 7.2796 (1.8); 7.2750 (1.5); 7.2734 (1.4); 7.2683(5.0); 7.2638 (5.2); 7.2592 (30.7); 7.2518 (1.8); 7.2491 (1.8); 7.2471(1.7); 7.2435 (2.1); 7.1409 (1.0); 7.1392 (1.1); 7.1375 (1.2); 7.1181(1.7); 7.1023 (0.7); 7.1006 (0.8); 7.0990 (0.7); 7.0117 (1.2); 7.0084(1.1); 6.9909 (1.1); 6.9871 (1.8); 6.9834 (1.1); 6.9659 (1.0); 6.9627(0.9); 4.8954 (16.0); 4.2908 (2.0); 4.2729 (6.3); 4.2551 (6.4); 4.2373(2.1); 2.1688 (1.5); 1.5705 (3.9); 1.3044 (7.6); 1.2866 (15.5); 1.2687(7.5); 1.2565 (0.6); −0.0002 (10.8) I-059: ¹H-NMR(601.6 MHz, CD3CN): δ =7.4173 (0.4); 7.4144 (0.6); 7.4090 (0.5); 7.4059 (0.8); 7.4049 (0.8);7.4007 (1.9); 7.3968 (1.2); 7.3954 (0.9); 7.3935 (1.1); 7.3924 (1.1);7.3874 (2.5); 7.3847 (1.6); 7.3800 (1.0); 7.3743 (1.3); 7.3717 (0.9);7.3492 (0.8); 7.3468 (1.1); 7.3407 (2.5); 7.3385 (5.6); 7.3354 (2.9);7.3292 (1.9); 7.3266 (3.6); 7.3256 (3.4); 7.3213 (0.7); 7.3201 (0.8);7.3172 (1.1); 7.3143 (0.5); 7.3116 (0.7); 7.2409 (3.8); 7.2398 (4.1);7.2387 (4.1); 7.2265 (4.1); 7.2142 (0.9); 7.2132 (0.9); 7.1210 (1.0);7.1194 (1.0); 7.1071 (1.0); 7.1041 (1.4); 7.1019 (1.1); 7.0900 (1.0);7.0882 (1.0); 4.8184 (16.0); 4.1925 (2.0); 4.1806 (6.0); 4.1688 (6.1);4.1569 (2.0); 2.0980 (6.3); 1.9225 (0.4); 1.9182 (0.5); 1.9145 (3.5);1.9104 (6.2); 1.9062 (9.3); 1.9022 (6.5); 1.8981 (3.3); 1.2109 (7.1);1.1990 (14.5); 1.1872 (7.1) I-060: ¹H-NMR(601.6 MHz, CD3CN): δ = 7.4611(0.5); 7.4582 (0.7); 7.4511 (1.3); 7.4483 (1.9); 7.4467 (1.5); 7.4372(3.5); 7.4242 (3.7); 7.4191 (1.0); 7.4150 (1.6); 7.4124 (2.9); 7.4096(2.0); 7.4065 (3.0); 7.4040 (1.8); 7.3968 (1.9); 7.3943 (4.6); 7.3862(0.8); 7.3833 (1.6); 7.3797 (1.3); 7.3410 (3.9); 7.3388 (4.2); 7.3360(2.1); 7.3312 (1.2); 7.3278 (3.0); 7.3250 (2.4); 7.2759 (1.2); 7.2635(1.9); 7.2621 (1.8); 7.2511 (0.8); 7.1598 (1.2); 7.1579 (1.0); 7.1454(1.2); 7.1428 (1.6); 7.1278 (0.9); 4.8860 (16.0); 4.4421 (0.6); 4.2520(2.0); 4.2401 (5.9); 4.2283 (5.9); 4.2165 (2.0); 4.1374 (0.4); 4.1257(0.4); 2.1602 (655.3); 2.1329 (0.4); 2.0871 (0.5); 2.0831 (0.8); 2.0790(1.2); 2.0749 (0.8); 2.0707 (0.4); 1.9927 (4.6); 1.9846 (10.1); 1.9804(13.4); 1.9766 (81.7); 1.9725 (144.5); 1.9684 (199.9); 1.9642 (135.7);1.9601 (71.1); 1.8618 (0.4); 1.8577 (0.8); 1.8536 (1.2); 1.8496 (0.8);1.8454 (0.4); 1.3017 (1.4); 1.2717 (7.1); 1.2599 (14.8); 1.2481 (7.0);1.1792 (0.5); 1.1673 (1.0); 1.1555 (0.5); 0.0606 (0.4) I-061:¹H-NMR(300.1 MHz, CDCl3): δ = 7.4164 (0.3); 7.4114 (0.3); 7.4078 (0.5);7.4023 (0.5); 7.3941 (1.2); 7.3829 (1.1); 7.3748 (1.9); 7.3719 (2.1);7.3652 (2.3); 7.3613 (2.1); 7.3576 (1.6); 7.3508 (2.0); 7.3467 (2.0);7.3447 (2.0); 7.3380 (3.2); 7.3351 (2.7); 7.3242 (1.4); 7.3164 (2.0);7.3078 (3.2); 7.2993 (1.9); 7.2967 (1.4); 7.2883 (0.6); 7.2808 (1.1);7.2741 (0.8); 7.2602 (3.6); 7.2124 (0.8); 7.2103 (0.8); 7.1861 (1.1);7.1609 (0.4); 7.1591 (0.4); 7.0860 (0.7); 7.0824 (0.6); 7.0580 (0.7);7.0534 (1.1); 7.0491 (0.7); 7.0254 (0.6); 7.0219 (0.5); 5.2451 (0.5);5.2218 (1.6); 5.1986 (1.7); 5.1754 (0.5); 3.7711 (16.0); 2.0412 (0.9);1.6902 (6.7); 1.6670 (6.6); 1.5789 (1.0); 1.2570 (0.6); −0.0001 (2.8)I-062: ¹H-NMR(300.1 MHz, CDCl3): δ = 7.2640 (0.6); 7.2493 (1.7); 7.2200(4.6); 7.1952 (7.9); 7.1898 (8.1); 7.1777 (7.5); 7.0497 (1.4); 7.0249(1.9); 6.9986 (0.8); 6.9475 (1.1); 6.9158 (1.6); 6.8870 (0.9); 4.8826(9.9); 3.7244 (16.0); 3.6578 (15.8); 1.5397 (0.4); 1.1862 (0.6); 0.0002(5.8); −0.0709 (2.0) I-063: ¹H-NMR(300.1 MHz, CDCl3): δ = 7.3913 (0.6);7.3857 (0.7); 7.3649 (1.5); 7.3594 (1.9); 7.3263 (6.4); 7.3138 (6.3);7.3073 (3.8); 7.2861 (1.8); 7.2600 (18.4); 7.2391 (0.4); 7.2246 (0.4);7.1861 (1.0); 7.1607 (1.4); 7.1348 (0.6); 7.0591 (0.8); 7.0265 (1.3);6.9982 (0.8); 4.9254 (9.2); 3.7975 (16.0); 3.1683 (5.1); 2.0437 (1.0);1.5555 (6.5); 1.2822 (0.7); 1.2550 (4.4); 1.2349 (0.4); 0.8807 (0.3);0.0696 (1.2); −0.0001 (14.4); −0.0108 (0.5) I-064: ¹H-NMR(300.1 MHz,CDCl3): δ = 7.6138 (0.3); 7.3225 (9.6); 7.2594 (49.0); 7.1697 (3.7);7.0995 (2.9); 7.0707 (4.5); 7.0482 (1.9); 6.9081 (0.4); 5.2712 (0.7);5.2470 (2.0); 5.2242 (1.9); 5.2028 (0.7); 3.7824 (16.0); 1.7600 (0.3);1.6946 (8.0); 1.6712 (7.7); 1.6536 (0.7); 1.5499 (68.6); 1.3134 (0.4);1.2583 (1.7); 0.8833 (0.3); 0.8586 (0.4); 0.0686 (4.2); −0.0006 (41.4)I-065: ¹H-NMR(300.1 MHz, CDCl3): δ = 7.2888 (0.4); 7.2713 (2.4); 7.2591(19.5); 7.2537 (4.9); 7.2415 (6.3); 7.2347 (5.3); 7.2243 (2.9); 7.1085(2.7); 7.0987 (1.8); 7.0942 (1.7); 7.0826 (2.0); 7.0758 (1.6); 7.0495(2.2); 7.0207 (3.7); 6.9915 (1.7); 4.9778 (9.0); 3.8115 (16.0); 3.7362(16.0); 2.0422 (0.6); 1.5567 (4.7); 1.2580 (0.7); 0.0106 (0.9); −0.0001(14.4); −0.0110 (0.5) I-066: ¹H-NMR(300.1 MHz, CDCl3): δ = 7.3529 (1.6);7.3352 (2.0); 7.3231 (2.6); 7.3129 (1.4); 7.3054 (2.8); 7.3002 (2.6);7.2807 (2.6); 7.2740 (5.3); 7.2596 (44.7); 7.2331 (0.8); 7.2189 (0.4);7.2069 (0.4); 7.1766 (2.5); 7.1697 (2.3); 7.1491 (1.9); 7.1440 (1.6);7.0685 (0.4); 7.0591 (2.0); 7.0302 (3.4); 7.0009 (1.6); 5.5336 (0.3);4.9415 (8.8); 3.8057 (16.0); 3.1592 (5.4); 1.5404 (12.3); 1.5124 (2.2);1.2547 (2.6); 0.0106 (1.8); −0.0001 (35.9); −0.0110 (1.6) I-067:¹H-NMR(300.1 MHz, CDCl3): δ = 7.4439 (0.4); 7.4248 (0.5); 7.4170 (0.8);7.3992 (0.7); 7.3969 (0.7); 7.3904 (0.7); 7.3714 (0.6); 7.3061 (0.5);7.2854 (0.6); 7.2785 (1.1); 7.2600 (12.0); 7.2516 (1.0); 7.2310 (0.7);7.1975 (0.4); 7.1942 (0.6); 7.1890 (0.5); 7.1858 (0.6); 7.1695 (0.8);7.1664 (1.1); 7.1583 (2.0); 7.1554 (1.4); 7.1532 (1.5); 7.1499 (0.9);7.1413 (0.5); 7.1380 (0.6); 7.1331 (1.2); 7.1296 (1.4); 7.1279 (1.3);7.1245 (0.8); 7.0701 (0.5); 7.0670 (0.5); 7.0618 (0.6); 7.0587 (0.6);7.0425 (0.8); 7.0395 (0.8); 7.0342 (1.0); 7.0311 (1.0); 7.0250 (0.8);7.0191 (0.9); 7.0158 (1.0); 7.0117 (1.0); 7.0066 (0.6); 7.0034 (0.6);6.9949 (1.4); 6.9881 (1.8); 6.9809 (1.1); 6.9640 (0.7); 6.9569 (1.0);6.9494 (0.6); 6.9025 (1.0); 6.8987 (0.8); 6.8779 (0.8); 6.8757 (0.8);6.8722 (0.8); 5.2616 (0.5); 5.2383 (1.6); 5.2151 (1.6); 5.1918 (0.5);3.7919 (16.0); 1.7023 (6.5); 1.6790 (6.4); 1.5453 (6.2); 0.0107 (0.4);−0.0001 (9.8); −0.0037 (1.6); −0.0111 (0.3) I-068: ¹H-NMR(300.1 MHz,CDCl3): δ = 7.3751 (0.4); 7.3550 (0.6); 7.3481 (0.9); 7.3287 (1.0);7.3222 (0.8); 7.3024 (0.8); 7.2600 (16.6); 7.2204 (0.4); 7.1935 (1.0);7.1726 (1.2); 7.1668 (0.8); 7.1439 (1.2); 7.1204 (1.0); 7.1149 (1.0);7.0921 (0.5); 7.0868 (0.5); 7.0642 (1.5); 7.0354 (1.9); 7.0050 (0.9);7.0004 (1.0); 6.9734 (0.6); 6.9678 (0.8); 6.9651 (0.7); 6.9399 (2.2);6.9273 (0.6); 6.9100 (1.4); 6.9020 (1.2); 6.8951 (0.6); 6.8348 (1.2);6.8313 (1.1); 6.8061 (1.1); 4.9754 (8.1); 3.8212 (16.0); 3.7329 (15.7);1.5501 (4.4); 1.2572 (0.4); 0.0107 (0.6); −0.0001 (13.9); −0.0112 (0.5)I-069: ¹H-NMR(300.1 MHz, CDCl3): δ = 7.3714 (0.3); 7.3491 (0.8); 7.3309(0.8); 7.3210 (0.8); 7.3088 (0.4); 7.3010 (0.7); 7.2602 (29.7); 7.2400(1.2); 7.2167 (1.0); 7.2109 (0.8); 7.1892 (0.7); 7.1210 (4.2); 7.0922(2.7); 7.0652 (0.7); 6.9931 (2.2); 6.9679 (2.1); 6.9634 (2.3); 6.9441(0.9); 6.9021 (1.5); 6.8773 (1.0); 4.9367 (8.9); 3.8143 (16.0); 3.1835(5.5); 2.0440 (0.9); 1.5530 (16.2); 1.2826 (0.6); 1.2549 (3.6); 1.2353(0.3); 0.0700 (0.4); −0.0001 (21.8) I-070: ¹H-NMR(400.4 MHz, d₆-DMSO): δ= 7.4457 (6.7); 7.4389 (7.8); 7.4292 (7.0); 7.3610 (1.9); 7.3435 (5.3);7.3245 (4.8); 7.3061 (5.1); 7.3034 (5.7); 7.3003 (7.0); 7.2914 (5.8);7.2857 (5.4); 7.2677 (1.1); 7.1494 (4.0); 7.1457 (6.6); 7.1255 (4.8);4.9533 (14.0); 4.7640 (0.4); 4.2791 (0.4); 4.2199 (2.2); 4.2022 (6.9);4.1845 (7.0); 4.1667 (2.4); 3.3849 (0.5); 3.3349 (117.7); 2.6779 (1.5);2.6036 (0.5); 2.5588 (1.5); 2.5135 (168.7); 2.5090 (244.4); 2.5046(207.4); 2.3361 (1.4); 2.3319 (1.2); 1.9965 (0.9); 1.2472 (0.8); 1.2323(7.8); 1.2145 (16.0); 1.1968 (7.7); 1.1817 (0.7); 0.9624 (0.4); 0.9459(0.4); 0.8677 (1.0); 0.8594 (0.7); 0.8502 (0.6); 0.8406 (0.6); 0.8237(0.3) I-071: ¹H-NMR(400.4 MHz, d₆-DMSO): δ = 7.5293 (6.5); 7.5080 (7.8);7.3894 (2.0); 7.3849 (1.0); 7.3719 (5.6); 7.3526 (4.8); 7.3301 (9.7);7.3088 (9.1); 7.2899 (0.8); 7.1626 (6.0); 7.1447 (4.9); 4.9501 (14.5);4.7623 (0.7); 4.2779 (0.8); 4.2132 (2.2); 4.1955 (6.9); 4.1777 (7.0);4.1601 (2.3); 3.3367 (64.9); 2.6755 (1.3); 2.5106 (154.6); 2.5068(190.6); 2.5027 (133.8); 2.4574 (0.5); 2.3336 (1.3); 1.2368 (1.2);1.2261 (7.9); 1.2083 (16.0); 1.1906 (7.6) I-072: ¹H-NMR(400.2 MHz,d₆-DMSO): δ = 7.4958 (0.6); 7.4424 (7.8); 7.4346 (9.7); 7.4264 (8.5);7.3025 (4.8); 7.2961 (5.3); 7.2869 (4.7); 7.2005 (8.0); 7.1929 (8.8);7.1790 (15.0); 4.9380 (16.0); 4.7548 (0.6); 4.2687 (0.8); 4.2080 (2.6);4.1906 (7.1); 4.1729 (7.2); 4.1553 (2.5); 3.6598 (0.6); 3.5534 (0.7);3.5120 (0.8); 3.4784 (0.9); 3.4603 (1.2); 3.4199 (1.4); 3.3880 (2.1);3.3250 (971.4); 3.3223 (684.4); 3.2696 (1.7); 2.6694 (5.8); 2.6004(1.0); 2.5710 (1.3); 2.5003 (885.0); 2.4967 (826.3); 2.4405 (3.2);2.4169 (1.1); 2.3273 (5.9); 1.2313 (1.8); 1.2213 (7.7); 1.2036 (15.4);1.1858 (7.5) I-073: ¹H-NMR(400.3 MHz, d₆-DMSO): δ = 7.4684 (9.8); 7.4613(9.5); 7.4572 (7.5); 7.4456 (2.8); 7.4417 (3.0); 7.4310 (7.7); 7.4256(3.0); 7.4190 (3.3); 7.4134 (6.4); 7.4090 (7.4); 7.4011 (1.1); 7.3218(5.8); 7.3157 (5.4); 7.3106 (5.0); 7.3070 (5.0); 7.3032 (3.5); 7.2982(2.8); 7.1556 (8.6); 7.1502 (3.0); 7.1383 (5.5); 7.1335 (6.3); 4.9566(13.8); 4.2163 (2.2); 4.1986 (6.8); 4.1808 (6.8); 4.1631 (2.3); 3.3452(15.7); 3.3352 (56.3); 2.6800 (1.5); 2.6755 (1.5); 2.5109 (202.9);2.5066 (202.5); 2.5023 (126.4); 2.3380 (1.5); 2.3337 (1.5); 1.2393(1.9); 1.2290 (8.0); 1.2218 (3.4); 1.2113 (16.0); 1.2043 (2.2); 1.1936(7.4) I-074: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 7.5517 (6.3); 7.5307 (7.9);7.4582 (6.5); 7.4365 (7.6); 7.3490 (7.7); 7.3279 (6.5); 7.1765 (7.6);7.1548 (6.8); 4.9517 (13.8); 4.7590 (2.1); 4.2731 (2.3); 4.2107 (2.2);4.1930 (6.6); 4.1752 (6.7); 4.1576 (2.5); 4.1436 (0.9); 4.1259 (0.3);3.4327 (0.4); 3.3843 (1.9); 3.3348 (292.4); 2.6735 (1.1); 2.5083(131.3); 2.5046 (165.9); 2.5009 (127.3); 2.3314 (1.1); 1.2641 (0.6);1.2345 (3.5); 1.2244 (8.6); 1.2066 (16.0); 1.1889 (7.9); 1.1718 (0.9);0.8531 (0.6); 0.8357 (0.4) I-075: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4024(0.7); 7.3917 (0.6); 7.3849 (2.0); 7.3778 (0.8); 7.3712 (1.4); 7.3668(2.3); 7.3626 (1.4); 7.3539 (1.0); 7.3518 (0.9); 7.3495 (1.0); 7.3474(1.0); 7.3417 (2.7); 7.3375 (2.1); 7.3266 (2.0); 7.3223 (5.4); 7.3092(1.7); 7.3045 (4.1); 7.3019 (2.5); 7.2905 (5.6); 7.2875 (6.2); 7.2707(3.7); 7.2662 (2.9); 7.2599 (27.3); 7.1604 (1.2); 7.1415 (1.9); 7.1227(0.8); 7.0452 (1.2); 7.0421 (1.2); 7.0243 (1.1); 7.0209 (2.1); 7.0176(1.3); 6.9997 (1.0); 6.9965 (1.1); 5.2970 (9.0); 4.9859 (16.0); 4.2998(2.1); 4.2820 (6.4); 4.2641 (6.5); 4.2463 (2.1); 1.5482 (4.3); 1.3028(7.5); 1.2955 (0.8); 1.2849 (15.2); 1.2781 (0.7); 1.2671 (7.3); −0.0002(10.0) I-076: ¹H-NMR(400.3 MHz, d₆-DMSO): δ = 10.8519 (0.6); 7.3806(2.5); 7.3583 (5.7); 7.3446 (5.6); 7.3195 (5.3); 7.2973 (7.6); 7.2754(3.7); 7.2469 (1.6); 7.2246 (6.6); 7.2113 (8.0); 7.2041 (10.0); 7.1984(10.7); 4.9427 (14.5); 4.7619 (0.7); 4.2752 (0.8); 4.2120 (2.4); 4.1945(7.1); 4.1766 (7.6); 4.1590 (3.7); 4.1083 (1.0); 4.0954 (1.2); 4.0842(0.7); 3.4315 (0.6); 3.3318 (372.2); 3.2799 (1.5); 3.2247 (0.7); 3.1792(3.4); 3.1661 (3.1); 3.1088 (0.6); 3.0815 (0.7); 3.0416 (0.8); 3.0255(1.1); 2.9520 (1.1); 2.8550 (0.6); 2.6761 (6.7); 2.6068 (1.3); 2.5072(1051.7); 2.3992 (1.1); 2.3746 (0.8); 2.3341 (6.7); 2.2686 (0.6); 2.2217(0.6); 2.1319 (0.7); 1.5669 (0.7); 1.5031 (0.6); 1.4028 (0.7); 1.2668(1.3); 1.2262 (7.8); 1.2085 (16.0); 1.1908 (9.0); 1.0907 (1.0); 0.8812(0.6); 0.8563 (0.7); 0.8490 (0.7); −1.5794 (0.6); −3.1735 (0.6); −3.5033(0.6); −3.6659 (0.6); −3.8138 (0.6) I-077: ¹H-NMR(400.2 MHz, d₆-DMSO): δ= 7.5334 (6.0); 7.5121 (7.9); 7.3342 (7.8); 7.3128 (6.7); 7.2552 (1.3);7.2493 (0.8); 7.2327 (6.1); 7.2205 (7.0); 7.2125 (8.8); 7.2073 (8.8);7.1988 (2.0); 7.1849 (0.8); 7.1570 (0.3); 4.9418 (14.4); 4.7596 (0.4);4.2746 (0.5); 4.2085 (2.2); 4.1908 (6.9); 4.1730 (7.0); 4.1553 (2.3);3.3294 (39.3); 2.6732 (0.8); 2.5539 (1.4); 2.5088 (86.7); 2.5044(111.2); 2.5001 (82.8); 2.4537 (0.8); 2.3357 (0.5); 2.3312 (0.6); 1.2690(0.3); 1.2343 (3.4); 1.2221 (8.0); 1.2044 (16.0); 1.1866 (7.6); 0.8531(0.6) I-078: ¹H-NMR(400.3 MHz, d₆-DMSO): δ = 7.4489 (7.3); 7.4271 (8.8);7.3949 (2.6); 7.3791 (4.3); 7.3733 (6.1); 7.3596 (5.4); 7.3378 (5.4);7.3157 (7.5); 7.2940 (2.9); 7.1658 (8.3); 7.1443 (7.6); 4.9529 (16.0);4.2139 (2.4); 4.1963 (7.2); 4.1785 (7.4); 4.1609 (2.7); 3.3662 (0.4);3.3316 (94.9); 3.2939 (0.7); 3.1784 (0.9); 3.1658 (0.9); 2.6756 (1.6);2.5859 (0.3); 2.5069 (264.9); 2.3340 (1.6); 1.2279 (7.7); 1.2101 (15.2);1.1924 (8.0); 1.1509 (0.4) I-080: ¹H-NMR(400.4 MHz, d₆-DMSO): δ = 7.6418(0.9); 7.6268 (1.1); 7.6198 (1.9); 7.6048 (1.9); 7.5979 (1.2); 7.5828(1.0); 7.5179 (6.2); 7.5133 (2.8); 7.5014 (2.5); 7.4965 (8.2); 7.4267(1.0); 7.4200 (1.0); 7.3977 (1.5); 7.3939 (1.4); 7.3780 (1.0); 7.3712(1.0); 7.3249 (7.7); 7.3203 (3.0); 7.3083 (2.2); 7.3035 (6.5); 7.2411(0.8); 7.2214 (1.5); 7.1989 (0.8); 4.9214 (13.7); 4.1954 (2.2); 4.1777(6.9); 4.1599 (7.0); 4.1421 (2.2); 3.3332 (182.0); 2.6809 (0.8); 2.6765(1.2); 2.6718 (0.9); 2.5565 (0.5); 2.5298 (3.9); 2.5160 (65.0); 2.5118(140.8); 2.5074 (199.2); 2.5030 (154.0); 2.4987 (77.5); 2.3389 (0.8);2.3344 (1.2); 2.3300 (1.0); 1.9948 (0.8); 1.4029 (1.9); 1.2669 (0.9);1.2380 (1.1); 1.2067 (7.8); 1.1979 (0.9); 1.1890 (16.0); 1.1803 (1.1);1.1712 (7.5); 1.0921 (0.5); 0.9606 (0.8); 0.9440 (0.8); 0.8776 (0.4);0.8658 (1.0); 0.8573 (0.7); 0.8444 (0.6); 0.8387 (0.9); 0.8212 (0.5)I-081: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 7.6335 (0.9); 7.6185 (1.0);7.6115 (1.8); 7.5966 (1.8); 7.5895 (1.0); 7.5745 (0.9); 7.4070 (1.0);7.4000 (1.1); 7.3842 (1.3); 7.3805 (1.4); 7.3775 (1.4); 7.3738 (1.3);7.3649 (2.4); 7.3587 (1.9); 7.3512 (3.6); 7.3426 (4.1); 7.3348 (1.5);7.3290 (3.6); 7.3221 (0.4); 7.3001 (0.7); 7.2935 (4.2); 7.2877 (1.1);7.2764 (1.4); 7.2712 (6.1); 7.2656 (1.1); 7.2544 (0.9); 7.2490 (2.2);7.2323 (0.6); 7.2289 (0.7); 7.2252 (0.6); 7.2086 (1.2); 7.1897 (0.6);7.1861 (0.6); 7.1826 (0.5); 4.9151 (12.8); 4.7822 (0.8); 4.7586 (0.3);4.2701 (0.4); 4.1947 (2.1); 4.1769 (6.8); 4.1591 (6.8); 4.1414 (2.2);3.4235 (0.6); 3.3745 (0.8); 3.3625 (0.4); 3.3236 (429.6); 3.2988 (0.6);3.2936 (0.4); 3.2740 (0.8); 2.6787 (0.8); 2.6742 (1.0); 2.6697 (0.7);2.5277 (3.2); 2.5229 (5.0); 2.5142 (62.8); 2.5097 (132.0); 2.5052(180.0); 2.5006 (127.3); 2.4962 (58.8); 2.4611 (0.8); 2.3410 (0.4);2.3367 (0.8); 2.3321 (1.2); 2.3275 (0.8); 1.4017 (0.7); 1.2656 (0.6);1.2383 (0.7); 1.2325 (0.7); 1.2146 (1.0); 1.2061 (7.7); 1.1968 (0.9);1.1884 (16.0); 1.1706 (7.6); 1.0910 (0.4) I-082: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 13.0004 (0.8); 7.5268 (1.1); 7.5227 (1.4); 7.5076 (2.3);7.5032 (2.8); 7.4881 (1.4); 7.4838 (1.6); 7.4730 (0.7); 7.4686 (0.7);7.4603 (0.8); 7.4540 (1.3); 7.4488 (1.2); 7.4412 (1.3); 7.4368 (1.2);7.4337 (1.3); 7.4290 (1.0); 7.4208 (1.0); 7.4164 (0.9); 7.4047 (1.0);7.3952 (7.5); 7.3881 (7.2); 7.3787 (6.5); 7.3721 (2.0); 7.2953 (1.7);7.2926 (2.3); 7.2863 (1.0); 7.2798 (4.9); 7.2758 (5.2); 7.2736 (7.4);7.2681 (3.6); 7.2649 (5.9); 7.2557 (3.9); 7.2452 (1.8); 7.2403 (2.1);7.2369 (1.6); 7.2192 (1.3); 7.2161 (1.2); 4.8316 (0.9); 4.8209 (16.0);4.0382 (0.6); 4.0205 (0.6); 3.3141 (10.9); 2.5231 (1.4); 2.5184 (2.0);2.5097 (20.0); 2.5052 (40.9); 2.5006 (55.8); 2.4961 (38.8); 2.4916(17.6); 1.9876 (2.5); 1.2360 (0.8); 1.1920 (0.7); 1.1742 (1.4); 1.1564(0.7); 0.0080 (0.6); −0.0002 (19.0); −0.0085 (0.6) I-083: ¹H-NMR(400.0MHz, CDCl3): δ = 7.6410 (2.5); 7.6207 (2.9); 7.4145 (2.8); 7.3943 (2.5);7.2592 (32.4); 7.1139 (1.5); 7.1084 (0.8); 7.1020 (1.8); 7.0967 (1.3);7.0912 (2.5); 7.0851 (1.0); 7.0793 (2.4); 7.0025 (2.3); 6.9967 (0.8);6.9908 (0.5); 6.9821 (2.8); 6.9653 (0.7); 6.9596 (1.6); 4.9345 (9.3);3.8483 (0.6); 3.8148 (16.0); 3.8015 (0.8); 1.5409 (0.7); 1.2546 (0.7);1.0706 (0.9); −0.0002 (12.2); −0.0084 (0.7) I-084: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.4709 (1.1); 7.4545 (1.2); 7.4384 (0.8); 7.3819 (0.8);7.3639 (1.8); 7.3463 (1.4); 7.2734 (1.9); 7.2595 (17.6); 7.2337 (3.1);7.2098 (1.4); 5.2978 (0.6); 4.8440 (10.3); 3.7706 (16.0); 2.7713 (0.6);1.5422 (1.7); 1.2429 (0.5); −0.0002 (6.2) I-085: ¹H-NMR(400.3 MHz,d₆-DMSO): δ = 7.5852 (1.9); 7.5689 (2.7); 7.5642 (2.6); 7.5481 (2.7);7.5264 (1.0); 7.4298 (2.2); 7.4245 (2.2); 7.4054 (3.9); 7.4001 (3.4);7.3865 (4.8); 7.3815 (4.5); 7.3688 (7.4); 7.3531 (4.1); 7.3492 (4.8);7.3199 (3.5); 7.3073 (2.6); 7.3022 (3.6); 7.2814 (2.5); 7.2600 (2.9);7.2373 (1.2); 7.1615 (7.2); 7.1579 (7.4); 7.1438 (4.7); 7.1401 (4.7);5.0105 (0.9); 4.9852 (4.0); 4.9678 (11.3); 4.2777 (0.4); 4.2562 (0.4);4.2192 (3.7); 4.2013 (7.9); 4.1836 (7.0); 4.1660 (2.1); 3.4369 (0.6);3.3826 (10.3); 3.3562 (50.7); 3.3419 (98.1); 3.3364 (183.0); 3.2985(0.8); 3.0350 (0.4); 2.9853 (0.4); 2.9509 (0.4); 2.9008 (0.3); 2.8834(0.3); 2.7341 (0.5); 2.7272 (0.5); 2.7144 (0.6); 2.6801 (3.4); 2.6757(3.4); 2.6055 (1.4); 2.5505 (52.5); 2.5113 (502.8); 2.5067 (493.7);2.5027 (303.6); 2.4041 (0.6); 2.3779 (0.5); 2.3382 (3.3); 2.3337 (3.3);1.2275 (10.4); 1.2156 (8.8); 1.2097 (16.0); 1.1980 (4.0); 1.1920 (7.2);1.1541 (0.7); 0.8615 (0.3) I-086: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 7.5866(0.9); 7.5702 (1.1); 7.5653 (1.7); 7.5493 (1.7); 7.5443 (1.1); 7.5281(1.0); 7.4279 (1.0); 7.4217 (1.0); 7.4023 (1.3); 7.3983 (1.4); 7.3793(0.9); 7.3727 (0.9); 7.2782 (1.0); 7.2736 (0.9); 7.2572 (1.7); 7.2512(2.5); 7.2439 (0.8); 7.2348 (1.7); 7.2276 (5.5); 7.2222 (1.5); 7.2127(5.4); 7.2071 (6.4); 7.2033 (2.9); 7.1995 (5.7); 7.1906 (1.2); 7.1836(0.5); 7.1770 (0.6); 4.9798 (0.3); 4.9573 (10.3); 4.7572 (0.7); 4.2696(0.9); 4.2138 (2.0); 4.1960 (6.4); 4.1783 (6.4); 4.1606 (2.3); 4.1430(0.3); 3.3684 (0.6); 3.3623 (0.6); 3.3599 (0.6); 3.3425 (4.7); 3.3360(1.9); 3.3181 (360.9); 3.3051 (1.6); 3.3038 (1.4); 3.3025 (1.3); 3.3012(1.3); 3.3000 (1.3); 3.2937 (3.9); 2.6810 (1.0); 2.6765 (2.2); 2.6719(3.0); 2.6673 (2.2); 2.6628 (1.1); 2.5662 (1.3); 2.5256 (18.4); 2.5209(19.4); 2.5120 (161.2); 2.5075 (344.7); 2.5029 (469.2); 2.4984 (332.3);2.4938 (151.3); 2.4799 (10.9); 2.3389 (1.0); 2.3344 (2.1); 2.3298 (2.9);2.3253 (2.0); 1.2349 (0.7); 1.2227 (7.6); 1.2049 (16.0); 1.1872 (7.3)I-087: ¹H-NMR(400.4 MHz, d₆-DMSO): δ = 7.6065 (0.8); 7.5903 (1.0);7.5852 (1.7); 7.5691 (1.7); 7.5642 (1.1); 7.5480 (0.9); 7.4688 (0.6);7.4610 (6.4); 7.4556 (2.9); 7.4485 (1.3); 7.4443 (2.4); 7.4389 (7.9);7.4312 (2.2); 7.4251 (1.5); 7.4060 (1.0); 7.3996 (1.0); 7.3022 (0.8);7.2970 (0.8); 7.2811 (1.5); 7.2756 (1.4); 7.2597 (0.8); 7.2547 (0.7);7.1886 (0.8); 7.1810 (7.4); 7.1756 (2.2); 7.1641 (2.0); 7.1588 (6.4);7.1511 (0.7); 4.9731 (9.8); 4.2754 (0.4); 4.2196 (2.0); 4.2019 (6.4);4.1841 (6.5); 4.1664 (2.1); 3.3273 (115.4); 2.6809 (0.6); 2.6762 (0.9);2.6717 (0.6); 2.5298 (2.9); 2.5250 (4.4); 2.5163 (49.8); 2.5119 (106.9);2.5073 (147.4); 2.5028 (106.8); 2.4983 (50.9); 2.4621 (0.5); 2.4577(0.5); 2.3433 (0.3); 2.3389 (0.7); 2.3343 (0.9); 2.3297 (0.7); 1.2430(0.9); 1.2281 (7.7); 1.2104 (16.0); 1.1926 (7.3) I-088: ¹H-NMR(400.2MHz, d₆-DMSO): δ = 7.5608 (0.9); 7.5459 (1.0); 7.5388 (1.7); 7.5239(1.8); 7.5168 (1.0); 7.5019 (0.9); 7.4849 (0.9); 7.4686 (1.1); 7.4637(1.7); 7.4476 (1.8); 7.4426 (1.2); 7.4266 (2.3); 7.4224 (1.7); 7.4030(2.7); 7.4009 (2.7); 7.3966 (2.5); 7.3804 (1.3); 7.3779 (1.4); 7.3734(1.4); 7.2170 (1.1); 7.2108 (1.6); 7.2033 (1.0); 7.1957 (2.0); 7.1906(2.8); 7.1745 (1.0); 7.1705 (1.3); 7.1680 (1.3); 4.9293 (12.7); 4.1977(2.1); 4.1800 (6.7); 4.1622 (6.9); 4.1444 (2.2); 3.3772 (0.7); 3.3629(0.3); 3.3264 (227.7); 3.2910 (0.4); 3.2883 (0.4); 3.2770 (0.6); 2.6831(0.5); 2.6788 (0.9); 2.6742 (1.3); 2.6697 (0.9); 2.5606 (0.6); 2.5561(0.8); 2.5515 (0.8); 2.5464 (0.7); 2.5276 (5.4); 2.5226 (8.4); 2.5142(76.5); 2.5097 (155.6); 2.5052 (209.3); 2.5007 (149.9); 2.4962 (71.4);2.4561 (0.7); 2.4514 (0.4); 2.3366 (0.9); 2.3321 (1.3); 2.3275 (0.9);1.2400 (0.4); 1.2073 (7.7); 1.1896 (16.0); 1.1719 (7.5) I-089:¹H-NMR(400.2 MHz, d₆-DMSO): δ = 7.3952 (1.5); 7.3912 (1.7); 7.3742(6.8); 7.3591 (4.4); 7.3554 (6.0); 7.3149 (0.3); 7.2859 (2.6); 7.2717(4.0); 7.2638 (5.4); 7.2550 (3.1); 7.2501 (4.7); 7.2266 (5.2); 7.2045(7.0); 7.1871 (1.7); 7.1825 (2.4); 7.0328 (2.1); 7.0112 (4.8); 7.0069(4.2); 6.9917 (2.6); 6.9854 (3.3); 4.8806 (15.7); 4.1879 (2.4); 4.1701(7.4); 4.1524 (7.4); 4.1347 (2.4); 3.4614 (0.9); 3.4361 (27.6); 3.3768(0.4); 3.3704 (0.4); 3.3271 (178.3); 2.6775 (0.8); 2.6732 (0.9); 2.5488(0.6); 2.5085 (135.6); 2.5043 (155.1); 2.5003 (105.1); 2.3352 (0.8);2.3313 (0.9); 1.2382 (1.0); 1.2062 (8.3); 1.1884 (16.0); 1.1708 (7.7)I-090: ¹H-NMR(400.3 MHz, d₆-DMSO): δ = 7.4603 (3.2); 7.4537 (6.8);7.4487 (2.4); 7.4370 (4.7); 7.4323 (7.5); 7.4261 (0.9); 7.4077 (1.4);7.4034 (1.7); 7.3910 (4.7); 7.3870 (5.6); 7.3721 (3.9); 7.3679 (4.8);7.2576 (3.9); 7.2511 (8.1); 7.2460 (2.2); 7.2345 (4.0); 7.2298 (5.8);7.2231 (0.6); 7.0456 (2.0); 7.0428 (1.8); 7.0266 (4.4); 7.0237 (4.8);7.0195 (3.7); 7.0110 (1.5); 7.0045 (2.6); 6.9978 (2.7); 4.8881 (13.5);4.1923 (2.3); 4.1814 (2.9); 4.1744 (6.7); 4.1637 (2.9); 4.1567 (6.8);4.1390 (2.2); 4.0273 (0.3); 3.6148 (0.6); 3.5402 (0.3); 3.4429 (10.8);3.4362 (25.5); 3.3948 (0.6); 3.3878 (0.8); 3.3800 (1.0); 3.3729 (1.5);3.3371 (214.4); 3.3300 (520.8); 3.3160 (3.0); 3.3083 (1.5); 3.3002(0.7); 3.2962 (1.0); 3.2797 (0.4); 3.2308 (0.4); 3.0561 (0.4); 3.0106(0.5); 2.9816 (0.6); 2.9511 (0.6); 2.9453 (0.5); 2.6819 (4.5); 2.6778(4.8); 2.6733 (3.2); 2.6168 (0.5); 2.5857 (0.4); 2.5132 (713.7); 2.5088(763.9); 2.5044 (482.6); 2.5001 (194.1); 2.4792 (3.2); 2.4634 (1.4);2.4590 (1.5); 2.4544 (1.4); 2.4192 (1.0); 2.3767 (0.4); 2.3402 (4.4);2.3358 (4.8); 2.3312 (3.0); 1.9964 (0.8); 1.7669 (0.5); 1.2690 (0.8);1.2456 (1.7); 1.2172 (2.9); 1.2101 (7.8); 1.1996 (6.1); 1.1924 (16.0);1.1818 (3.4); 1.1747 (7.2); 0.8686 (0.4); 0.8613 (0.5) I-091:¹H-NMR(400.3 MHz, d₆-DMSO): δ = 7.3739 (7.3); 7.3583 (8.7); 7.3408(3.4); 7.3314 (2.0); 7.2935 (1.5); 7.2749 (2.5); 7.2569 (2.4); 7.2362(1.0); 7.1114 (2.2); 7.0910 (3.2); 7.0698 (1.6); 7.0360 (3.1); 7.0173(4.6); 6.9953 (3.8); 6.9894 (4.7); 6.9680 (3.4); 4.9007 (16.0); 4.1981(3.9); 4.1805 (8.2); 4.1628 (7.4); 4.1451 (2.4); 3.4607 (25.7); 3.4256(0.4); 3.3323 (60.6); 3.3017 (0.4); 2.6821 (1.1); 2.5128 (136.3); 2.5089(136.9); 2.4748 (1.1); 2.4697 (1.0); 2.3359 (1.0); 1.2140 (10.2); 1.1962(16.0); 1.1785 (7.2) I-092: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 7.3816(1.2); 7.3774 (1.6); 7.3586 (8.0); 7.3520 (6.0); 7.3433 (8.0); 7.3397(9.9); 7.3360 (7.4); 7.2377 (0.6); 7.2276 (3.5); 7.2239 (2.3); 7.2201(3.1); 7.2176 (2.6); 7.2142 (2.4); 7.2108 (2.7); 7.2036 (2.4); 7.0217(1.5); 7.0189 (1.7); 7.0027 (2.4); 7.0001 (3.1); 6.9953 (2.6); 6.9925(2.5); 6.9836 (1.3); 6.9808 (1.7); 6.9731 (2.5); 5.7580 (1.8); 4.8805(13.4); 4.1892 (2.1); 4.1715 (6.6); 4.1537 (6.7); 4.1360 (2.2); 3.4296(0.4); 3.4030 (25.5); 3.3802 (2.7); 3.3701 (0.7); 3.3545 (1.7); 3.3298(523.0); 3.2975 (0.7); 3.2934 (0.8); 3.2848 (1.2); 3.2792 (2.6); 3.2723(0.5); 2.6769 (0.8); 2.6724 (1.1); 2.6679 (0.8); 2.5541 (1.4); 2.5258(3.8); 2.5209 (5.9); 2.5124 (63.4); 2.5079 (131.9); 2.5034 (179.4);2.4989 (128.1); 2.4944 (60.1); 2.4536 (1.6); 2.3349 (0.9); 2.3304 (1.2);2.3258 (0.8); 1.2394 (1.1); 1.2075 (7.6); 1.1898 (16.0); 1.1721 (7.4)I-093: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3830 (0.5); 7.3789 (0.9); 7.3771(0.9); 7.3712 (5.9); 7.3668 (5.6); 7.3599 (2.3); 7.3577 (2.0); 7.3532(3.3); 7.3518 (2.8); 7.3448 (0.9); 7.3410 (1.1); 7.2799 (0.9); 7.2710(3.8); 7.2666 (4.2); 7.2595 (24.7); 7.2554 (3.0); 7.2466 (2.8); 7.2434(1.2); 7.2387 (1.0); 7.2354 (1.1); 7.2185 (0.7); 6.9026 (0.7); 6.8852(0.8); 6.8786 (1.3); 6.8612 (1.3); 6.8550 (0.8); 6.8377 (0.7); 5.2973(3.1); 4.8815 (16.0); 4.8074 (3.9); 4.3030 (2.0); 4.2852 (6.3); 4.2674(6.5); 4.2498 (2.5); 4.2332 (1.5); 1.5462 (0.9); 1.3149 (7.8); 1.2970(16.0); 1.2869 (2.1); 1.2792 (7.6); 1.2690 (3.9); 1.2512 (1.9); −0.0002(10.0) I-094: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4347 (0.5); 7.4326 (0.5);7.4283 (0.6); 7.4203 (0.5); 7.4136 (1.1); 7.4084 (0.9); 7.3949 (1.3);7.3899 (1.0); 7.3751 (0.8); 7.3707 (0.7); 7.2598 (43.6); 7.2507 (0.9);7.2476 (1.0); 7.2459 (1.0); 7.2291 (1.2); 7.2104 (0.7); 7.1648 (0.7);7.1615 (0.6); 7.1440 (0.7); 7.1404 (1.2); 7.1369 (0.7); 7.1194 (0.6);7.1162 (0.6); 6.7312 (1.4); 6.7218 (2.0); 6.7117 (1.5); 6.3895 (1.7);6.3847 (1.7); 6.3791 (1.6); 6.3743 (1.6); 6.1771 (1.0); 4.9050 (0.5);4.8896 (8.9); 4.8481 (1.2); 4.8039 (1.4); 3.7940 (1.5); 3.7896 (16.0);3.7810 (2.7); 3.7746 (2.2); 2.9186 (14.2); −0.0002 (17.8); −0.0085 (0.6)I-095: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4131 (0.6); 7.4112 (0.5); 7.4004(1.0); 7.3962 (0.7); 7.3926 (0.6); 7.3847 (0.6); 7.3804 (1.6); 7.3766(0.8); 7.3617 (1.0); 7.3575 (0.6); 7.2594 (27.0); 7.2536 (1.1); 7.2386(0.7); 7.2371 (0.7); 7.2338 (1.0); 7.2185 (0.9); 7.2171 (1.0); 7.2155(1.0); 7.1518 (0.7); 7.1486 (0.6); 7.1310 (0.6); 7.1275 (1.1); 7.1240(0.6); 7.1064 (0.6); 7.1033 (0.5); 6.7232 (1.4); 6.7140 (1.8); 6.7131(1.8); 6.7038 (1.4); 6.3851 (1.7); 6.3803 (1.7); 6.3747 (1.6); 6.3699(1.6); 5.2978 (0.6); 4.8889 (9.0); 4.8440 (2.8); 3.7872 (16.0); 3.7705(5.0); −0.0002 (11.8) I-096: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5179 (0.5);7.3913 (0.6); 7.3860 (1.0); 7.3783 (4.6); 7.3746 (5.1); 7.3684 (2.0);7.3642 (1.7); 7.3600 (3.2); 7.3584 (2.8); 7.3512 (1.0); 7.3470 (1.1);7.3368 (0.6); 7.2912 (0.9); 7.2811 (0.6); 7.2739 (4.4); 7.2697 (4.7);7.2646 (2.8); 7.2590 (92.5); 7.2497 (3.9); 7.2293 (0.9); 6.9950 (0.5);6.9132 (0.7); 6.8958 (0.8); 6.8893 (1.2); 6.8720 (1.2); 6.8658 (0.8);6.8484 (0.7); 5.2981 (0.5); 4.9621 (16.0); 4.8889 (2.0); 2.0451 (0.8);1.3325 (1.8); 1.2842 (3.0); 1.2767 (1.2); 1.2552 (5.7); 1.2409 (0.7);0.8799 (0.8); 0.0079 (0.9); −0.0002 (40.4); −0.0085 (1.6) I-097:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3575 (0.9); 7.3418 (1.2); 7.3366 (1.9);7.3225 (2.0); 7.3166 (1.4); 7.3016 (1.9); 7.2814 (1.5); 7.2755 (1.3);7.2601 (27.9); 7.2592 (28.9); 7.2385 (1.3); 7.1043 (1.0); 7.0861 (1.7);7.0799 (2.0); 7.0651 (0.9); 7.0589 (1.0); 7.0270 (4.7); 7.0061 (3.2);6.9985 (2.1); 6.9276 (0.9); 6.9102 (1.0); 6.9041 (1.8); 6.8867 (1.8);6.8803 (1.2); 6.8629 (0.9); 5.2977 (0.5); 4.8779 (16.0); 4.3029 (2.0);4.2850 (6.0); 4.2672 (6.2); 4.2494 (2.2); 1.3148 (6.3); 1.2976 (12.6);1.2969 (12.7); 1.2797 (6.5); 1.2791 (6.5); 0.0007 (10.2); −0.0002 (10.6)I-098: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3715 (1.0); 7.3571 (1.0); 7.3499(1.6); 7.3354 (1.6); 7.3291 (1.7); 7.3141 (2.0); 7.3087 (1.7); 7.2941(1.5); 7.2904 (0.8); 7.2881 (0.8); 7.2742 (1.2); 7.2591 (31.0); 7.0780(0.6); 7.0755 (0.7); 7.0716 (0.8); 7.0692 (0.8); 7.0569 (1.1); 7.0539(1.2); 7.0481 (1.6); 7.0357 (0.6); 7.0332 (0.7); 7.0297 (1.9); 7.0267(2.7); 7.0237 (1.6); 7.0142 (1.2); 7.0101 (3.1); 7.0055 (3.0); 6.9901(1.3); 6.9861 (1.2); 6.9800 (0.8); 6.9372 (0.6); 6.9335 (0.6); 6.9304(0.7); 6.9267 (0.7); 6.9180 (0.7); 6.9146 (1.1); 6.9112 (1.2); 6.9078(1.2); 6.9045 (0.7); 6.8958 (0.6); 6.8921 (0.6); 6.8889 (0.6); 6.8852(0.6); 6.8178 (1.1); 6.8109 (0.9); 6.7967 (1.1); 6.7930 (1.2); 6.7900(1.1); 6.7862 (1.0); 6.7721 (1.0); 6.7652 (0.9); 4.8831 (16.0); 4.2944(2.0); 4.2765 (6.3); 4.2587 (6.4); 4.2409 (2.1); 1.3054 (7.5); 1.2876(15.3); 1.2697 (7.4); −0.0002 (11.4) I-099: ¹H-NMR(400.0 MHz, CDCl3): δ= 8.2827 (0.5); 8.2799 (0.5); 8.2771 (0.5); 8.2623 (0.8); 8.2592 (0.8);8.2565 (0.6); 8.2084 (3.4); 8.2034 (1.0); 8.1912 (1.1); 8.1861 (3.6);8.1512 (0.8); 8.1466 (1.1); 8.1418 (0.6); 7.6937 (0.6); 7.6742 (0.8);7.6707 (0.7); 7.6360 (0.6); 7.5872 (1.0); 7.5668 (1.4); 7.5472 (0.7);7.5188 (0.8); 7.5133 (0.6); 7.5077 (3.0); 7.5031 (1.2); 7.4905 (1.1);7.4856 (2.7); 7.4176 (0.9); 7.4129 (0.7); 7.4101 (0.8); 7.4078 (0.7);7.3999 (1.4); 7.3973 (1.3); 7.3846 (1.1); 7.3810 (1.4); 7.3766 (0.9);7.3690 (0.8); 7.3647 (1.3); 7.3469 (0.8); 7.3423 (0.8); 7.2890 (0.7);7.2599 (100.1); 7.2425 (0.6); 7.2350 (0.7); 7.2213 (1.0); 7.2150 (1.0);7.1979 (0.5); 7.0625 (0.7); 7.0594 (0.7); 7.0416 (0.7); 7.0381 (1.2);7.0346 (0.8); 7.0316 (0.5); 7.0282 (0.8); 7.0169 (0.7); 7.0139 (0.7);6.9958 (0.6); 5.2986 (12.4); 5.0260 (6.6); 5.0221 (9.1); 5.0070 (0.6);4.9412 (3.2); 3.8380 (1.2); 3.8347 (0.5); 3.8264 (4.1); 3.8202 (12.1);3.8183 (16.0); 3.8108 (0.8); 3.7898 (1.2); 3.7746 (5.5); 3.6222 (0.5);0.0079 (1.1); −0.0002 (36.6); −0.0085 (1.1) I-100: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3504 (1.4); 7.3481 (1.1); 7.3439 (5.5); 7.3392 (5.4);7.3314 (3.4); 7.3298 (2.8); 7.3279 (3.5); 7.3264 (3.8); 7.3248 (3.2);7.3226 (1.3); 7.3188 (1.1); 7.3149 (2.5); 7.3071 (1.4); 7.3025 (0.7);7.2926 (1.1); 7.2728 (0.6); 7.2650 (3.6); 7.2587 (28.7); 7.2522 (2.4);7.2502 (1.8); 7.2487 (1.8); 7.2475 (1.8); 7.2460 (1.6); 7.2429 (1.5);7.2404 (2.4); 7.2353 (0.6); 6.9073 (0.6); 6.9035 (0.6); 6.9004 (0.6);6.8967 (0.7); 6.8880 (0.7); 6.8846 (1.0); 6.8812 (1.2); 6.8778 (1.1);6.8745 (0.7); 6.8658 (0.6); 6.8620 (0.6); 6.8589 (0.6); 6.8552 (0.6);6.7965 (0.9); 6.7896 (0.8); 6.7753 (1.0); 6.7718 (1.1); 6.7686 (1.0);6.7650 (0.9); 6.7507 (0.9); 6.7439 (0.8); 5.2966 (1.3); 4.8878 (14.8);4.2952 (1.9); 4.2774 (5.9); 4.2595 (6.0); 4.2417 (2.0); 1.3060 (7.7);1.2882 (16.0); 1.2703 (7.7); −0.0002 (10.6) I-101: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.2865 (0.8); 7.2822 (2.0); 7.2768 (1.0); 7.2693 (4.0);7.2656 (2.0); 7.2602 (19.7); 7.2547 (1.5); 7.2509 (3.0); 7.2489 (2.4);7.2470 (2.5); 7.2420 (0.9); 7.2379 (1.7); 7.2341 (1.0); 7.2206 (1.2);7.1328 (2.0); 7.1288 (2.9); 7.1232 (0.7); 7.1161 (1.0); 7.1115 (2.0);7.1085 (1.7); 7.0752 (2.1); 7.0697 (0.7); 7.0583 (0.6); 7.0534 (3.3);7.0485 (0.7); 7.0370 (0.6); 7.0317 (1.7); 4.9414 (9.1); 4.7549 (1.2);3.8129 (16.0); 3.7951 (1.3); 2.9544 (3.4); 2.8824 (2.9); 2.7669 (2.8);1.5676 (1.4); −0.0002 (6.1) I-102: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5185(0.6); 7.3767 (0.7); 7.3624 (0.9); 7.3575 (1.3); 7.3506 (0.5); 7.3436(0.9); 7.3424 (0.8); 7.3391 (1.1); 7.3379 (1.0); 7.3314 (0.8); 7.3300(0.5); 7.3232 (0.6); 7.3110 (0.6); 7.2695 (0.5); 7.2687 (0.6); 7.2679(0.7); 7.2671 (0.7); 7.2663 (0.8); 7.2655 (0.9); 7.2647 (1.1); 7.2638(1.5); 7.2596 (105.1); 7.2093 (0.8); 7.2075 (0.6); 7.2058 (0.7); 7.2043(0.6); 7.1899 (1.0); 7.1882 (1.0); 7.1863 (1.0); 7.1853 (0.9); 7.1689(0.5); 7.1485 (0.6); 7.1431 (0.6); 7.1391 (0.6); 7.1296 (0.6); 7.1243(0.7); 7.1212 (0.7); 7.1176 (1.0); 7.1141 (0.6); 7.1026 (0.6); 7.0975(1.2); 7.0928 (0.8); 7.0726 (0.7); 7.0559 (0.6); 7.0529 (0.6); 7.0352(0.6); 7.0315 (1.0); 7.0279 (0.6); 7.0098 (0.9); 7.0064 (0.9); 7.0008(0.5); 6.9991 (0.6); 6.9956 (1.1); 6.9938 (0.5); 4.9228 (1.0); 4.9118(8.1); 3.8066 (2.2); 3.8014 (16.0); 2.9618 (0.8); 2.9561 (2.2); 2.9552(2.3); 2.8845 (2.0); 2.8830 (2.0); 2.7731 (6.2); 1.5415 (8.4); 0.0079(1.4); 0.0046 (0.6); 0.0038 (0.7); 0.0021 (1.9); −0.0002 (44.3); −0.0028(2.2); −0.0043 (1.0); −0.0052 (0.7); −0.0060 (0.6); −0.0085 (1.3) I-104:¹H-NMR(400.6 MHz, CDCl3): δ = 7.4359 (0.5); 7.4215 (0.7); 7.4159 (0.9);7.4016 (0.9); 7.3956 (0.8); 7.3813 (0.7); 7.2972 (0.7); 7.2819 (1.1);7.2766 (1.7); 7.2604 (28.3); 7.2410 (1.0); 7.1907 (0.7); 7.1885 (0.7);7.1844 (0.7); 7.1822 (0.7); 7.1697 (1.1); 7.1675 (1.2); 7.1633 (1.2);7.1612 (1.2); 7.1551 (1.5); 7.1525 (1.5); 7.1512 (1.6); 7.1488 (1.4);7.1423 (0.8); 7.1400 (0.8); 7.1359 (1.2); 7.1334 (1.2); 7.1320 (1.2);7.1297 (0.8); 7.0635 (0.6); 7.0613 (0.6); 7.0572 (0.7); 7.0552 (0.6);7.0428 (1.0); 7.0407 (1.0); 7.0365 (1.1); 7.0346 (1.0); 7.0197 (1.3);7.0156 (1.4); 7.0093 (0.8); 6.9967 (1.2); 6.9906 (1.6); 6.9857 (1.6);6.9793 (0.8); 6.9670 (0.9); 6.9616 (1.2); 6.9559 (0.7); 6.8979 (1.1);6.8948 (1.0); 6.8790 (1.0); 6.8748 (0.9); 5.3002 (2.3); 5.2511 (0.5);5.2336 (1.7); 5.2162 (1.7); 5.1988 (0.5); 3.7933 (16.0); 1.7003 (6.8);1.6829 (6.7); 1.5400 (13.2); 0.0077 (2.4); −0.0002 (30.5); −0.0085 (1.6)I-107: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.0573 (0.5); 7.3503 (0.5); 7.3445(0.8); 7.3300 (0.8); 7.3256 (0.6); 7.3242 (0.6); 7.3102 (0.6); 7.2615(26.6); 7.1267 (1.6); 7.1210 (0.6); 7.1148 (1.7); 7.1096 (1.4); 7.1037(2.7); 7.0977 (0.7); 7.0955 (0.5); 7.0918 (2.6); 7.0884 (0.8); 7.0861(0.6); 7.0822 (1.0); 7.0444 (0.8); 7.0418 (1.0); 7.0406 (1.2); 7.0381(1.0); 7.0254 (0.9); 7.0230 (2.3); 7.0192 (1.5); 7.0015 (0.8); 6.9975(0.9); 6.9953 (0.7); 6.9914 (2.6); 6.9855 (0.6); 6.9741 (0.7); 6.9710(2.4); 6.9685 (1.8); 6.9653 (0.7); 6.9539 (0.5); 6.9482 (1.6); 4.9282(8.3); 3.8127 (16.0); 2.9762 (4.3); 2.8980 (3.9); 2.7690 (10.4); −0.0002(9.7) I-108: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3837 (0.5); 7.3774 (0.7);7.3758 (0.6); 7.3632 (0.8); 7.3583 (0.6); 7.3570 (0.6); 7.3435 (0.6);7.2628 (28.0); 7.1837 (0.6); 7.1812 (0.5); 7.1747 (0.5); 7.1625 (0.9);7.1598 (0.8); 7.1563 (0.7); 7.1536 (0.9); 7.1349 (0.6); 7.1266 (1.6);7.1208 (0.6); 7.1148 (1.7); 7.1093 (1.1); 7.1035 (2.3); 7.0977 (0.8);7.0954 (0.5); 7.0918 (2.2); 7.0739 (0.9); 7.0713 (1.0); 7.0700 (1.2);7.0675 (1.0); 7.0517 (2.2); 7.0485 (1.4); 7.0460 (0.8); 7.0305 (0.7);7.0264 (0.6); 7.0249 (0.7); 7.0202 (0.7); 7.0119 (2.4); 7.0059 (0.7);6.9945 (0.7); 6.9920 (2.5); 6.9889 (1.7); 6.9861 (0.7); 6.9748 (0.6);6.9690 (1.5); 5.2991 (1.3); 5.0251 (7.9); 4.9111 (0.8); 3.8219 (16.0);3.8069 (1.7); 3.0134 (14.3); 2.9409 (8.9); 2.0822 (9.8); −0.0002 (10.3)I-109: ¹H-NMR(400.0 MHz, CDCl3): δ = 8.0119 (1.2); 7.3489 (0.6); 7.3344(0.6); 7.2610 (55.1); 7.1087 (1.4); 7.1055 (0.6); 7.1030 (0.6); 7.0969(1.4); 7.0932 (0.8); 7.0910 (1.3); 7.0859 (2.2); 7.0798 (0.6); 7.0739(1.8); 7.0656 (0.5); 7.0380 (0.7); 7.0354 (0.8); 7.0341 (1.0); 7.0316(0.8); 7.0189 (0.6); 7.0162 (0.7); 7.0150 (1.0); 7.0125 (0.8); 7.0073(0.6); 7.0018 (0.5); 6.9971 (0.6); 6.9850 (0.7); 6.9801 (0.6); 6.9769(2.0); 6.9710 (0.6); 6.9597 (0.6); 6.9566 (1.9); 6.9539 (1.5); 6.9507(0.6); 6.9336 (1.3); 4.9215 (6.5); 3.8097 (12.6); 3.0090 (16.0); 2.9580(11.9); 2.9573 (12.6); 2.8825 (10.8); 2.8810 (11.0); 2.7716 (5.0);1.5585 (7.2); 0.0080 (0.7); −0.0002 (22.0); −0.0085 (0.6) I-110:¹H-NMR(400.0 MHz, CDCl3): δ = 8.0184 (0.8); 7.3499 (0.5); 7.3446 (0.8);7.3301 (0.8); 7.3255 (0.6); 7.3243 (0.6); 7.3104 (0.7); 7.2607 (33.5);7.1372 (1.6); 7.1314 (0.6); 7.1252 (1.7); 7.1199 (1.0); 7.1143 (2.3);7.1083 (1.0); 7.1065 (0.9); 7.1024 (2.6); 7.0879 (0.7); 7.0851 (0.8);7.0814 (0.6); 7.0789 (0.9); 7.0422 (0.9); 7.0395 (1.0); 7.0384 (1.3);7.0358 (1.0); 7.0224 (1.0); 7.0202 (2.2); 7.0167 (1.4); 7.0148 (0.9);7.0120 (0.5); 7.0003 (2.4); 6.9944 (1.3); 6.9884 (0.8); 6.9831 (0.8);6.9800 (2.5); 6.9775 (1.9); 6.9742 (0.7); 6.9629 (0.6); 6.9571 (1.6);4.9289 (8.6); 4.4776 (1.3); 3.8145 (16.0); 2.9550 (8.4); 2.8839 (7.1);2.8825 (7.2); 2.7698 (1.2); 2.7048 (3.0); 1.5641 (1.0); −0.0002 (12.6)I-111: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.2776 (3.1); 7.2708 (1.9); 7.2677(1.6); 7.2643 (3.9); 7.2577 (38.2); 7.2527 (5.0); 7.2487 (3.0); 7.2420(4.0); 7.2384 (2.8); 7.2343 (5.6); 7.2328 (4.8); 7.2315 (5.0); 7.2271(2.3); 7.2230 (0.9); 7.2168 (2.5); 7.2143 (1.4); 7.1259 (1.7); 7.1245(1.8); 7.1222 (1.3); 7.1091 (0.9); 7.1068 (1.3); 7.1054 (1.4); 7.0835(0.7); 7.0762 (6.4); 7.0710 (4.2); 7.0656 (1.5); 7.0597 (3.1); 7.0549(9.5); 7.0514 (4.6); 7.0431 (0.5); 7.0381 (1.6); 7.0328 (3.9); 7.0277(1.0); 7.0126 (0.6); 7.0103 (0.7); 7.0062 (0.5); 6.9910 (1.1); 6.9897(1.1); 6.9846 (0.9); 6.9833 (0.9); 6.9705 (0.5); 6.9681 (0.5); 5.2962(9.2); 5.2420 (9.9); 4.9865 (16.0); 1.5364 (4.1); −0.0002 (15.1) I-112:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3629 (1.4); 7.3566 (1.6); 7.3550 (1.0);7.3478 (2.4); 7.3451 (1.5); 7.3384 (2.7); 7.3346 (0.9); 7.3139 (1.1);7.3126 (1.0); 7.3095 (1.3); 7.3044 (8.2); 7.3006 (2.8); 7.2981 (5.7);7.2928 (2.2); 7.2908 (1.7); 7.2896 (2.0); 7.2876 (3.2); 7.2824 (0.7);7.2785 (0.8); 7.2712 (3.2); 7.2655 (2.4); 7.2567 (35.5); 7.2519 (4.1);7.2503 (5.0); 7.2489 (5.5); 7.2468 (2.2); 7.2440 (1.1); 7.2417 (2.3);7.2356 (5.8); 7.2320 (4.9); 7.2306 (5.6); 7.2258 (2.3); 7.2220 (1.0);7.2159 (1.5); 7.2129 (1.2); 7.0817 (0.6); 7.0746 (4.4); 7.0724 (4.4);7.0703 (2.2); 7.0686 (2.8); 7.0675 (3.4); 7.0620 (1.4); 7.0604 (1.1);7.0572 (2.3); 7.0531 (7.1); 7.0521 (6.7); 7.0478 (4.4); 7.0363 (1.0);7.0309 (2.9); 5.2951 (1.9); 5.2592 (11.4); 4.9721 (16.0); 1.5355 (5.4);−0.0002 (15.1) I-113: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.2884 (0.7); 7.2868(1.0); 7.2813 (3.8); 7.2773 (1.2); 7.2757 (1.5); 7.2726 (0.9); 7.2675(4.3); 7.2670 (4.5); 7.2651 (5.0); 7.2612 (3.4); 7.2586 (34.1); 7.2506(2.7); 7.2465 (6.6); 7.2391 (2.0); 7.2350 (2.8); 7.2311 (1.8); 7.2244(0.7); 7.2183 (1.5); 7.2174 (1.6); 7.1994 (0.6); 7.1317 (1.6); 7.1298(3.4); 7.1258 (4.5); 7.1201 (1.1); 7.1132 (1.8); 7.1107 (1.3); 7.1087(3.4); 7.1054 (2.7); 7.0753 (3.7); 7.0697 (1.1); 7.0610 (0.6); 7.0583(1.1); 7.0538 (5.2); 7.0484 (1.1); 7.0370 (0.9); 7.0316 (2.9); 5.9782(0.6); 5.9640 (1.2); 5.9520 (0.7); 5.9499 (0.7); 5.9379 (1.4); 5.9352(0.8); 5.9237 (0.7); 5.9210 (1.5); 5.9090 (0.8); 5.9069 (0.8); 5.8948(1.5); 5.8808 (0.8); 5.3723 (0.8); 5.3684 (2.1); 5.3648 (2.2); 5.3609(0.8); 5.3292 (0.7); 5.3254 (1.9); 5.3217 (1.9); 5.3179 (0.7); 5.2966(1.2); 5.2497 (0.9); 5.2465 (2.3); 5.2433 (2.2); 5.2401 (0.8); 5.2235(0.8); 5.2203 (2.2); 5.2171 (2.2); 5.2139 (0.8); 4.9592 (16.0); 4.7282(2.5); 4.7247 (4.0); 4.7211 (2.6); 4.7141 (2.5); 4.7106 (3.9); 4.7070(2.4); 1.5465 (1.1); −0.0002 (12.0) I-114: ¹H-NMR(400.0 MHz, CDCl3): δ =8.0183 (0.8); 7.4156 (0.6); 7.4140 (0.7); 7.4076 (4.0); 7.4034 (3.5);7.3967 (1.5); 7.3941 (1.3); 7.3897 (2.0); 7.3881 (1.8); 7.3811 (0.6);7.3773 (0.7); 7.3051 (2.3); 7.3007 (2.6); 7.2965 (0.7); 7.2946 (0.8);7.2933 (0.9); 7.2916 (0.8); 7.2892 (1.0); 7.2869 (1.0); 7.2807 (1.7);7.2603 (32.2); 7.1938 (0.5); 7.1781 (0.5); 7.1730 (1.1); 7.1574 (1.1);7.1526 (0.7); 7.1371 (0.6); 6.9576 (0.5); 6.9520 (1.0); 6.9467 (0.7);6.9327 (0.5); 6.9272 (1.0); 6.9211 (1.0); 6.9186 (0.6); 6.9001 (0.9);6.8978 (1.0); 6.8937 (0.7); 6.8914 (0.7); 6.8564 (0.8); 6.8541 (0.8);6.8513 (0.8); 6.8491 (0.7); 6.8361 (0.7); 6.8339 (0.7); 6.8310 (0.7);6.8288 (0.6); 4.9429 (8.7); 4.7599 (0.7); 3.8242 (16.0); 3.7970 (1.3);2.9554 (8.2); 2.8841 (7.3); 2.8826 (7.1); 2.7699 (1.3); 1.5731 (1.0);−0.0002 (13.4) I-115: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4102 (1.3); 7.4060(1.2); 7.3923 (0.7); 7.3908 (0.6); 7.2901 (0.8); 7.2858 (0.9); 7.2658(0.9); 7.2594 (33.9); 4.9363 (2.9); 3.8218 (5.6); 1.5379 (16.0); 0.0691(1.0); −0.0002 (14.1) I-116: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5185 (1.2);7.3437 (0.8); 7.3332 (8.5); 7.3299 (3.4); 7.3279 (4.9); 7.3251 (9.3);7.3207 (7.1); 7.3167 (9.3); 7.3078 (5.7); 7.3036 (2.8); 7.2983 (5.7);7.2909 (2.5); 7.2854 (5.5); 7.2781 (1.3); 7.2757 (1.0); 7.2751 (1.0);7.2742 (0.9); 7.2734 (1.0); 7.2726 (1.0); 7.2718 (1.0); 7.2710 (1.2);7.2702 (1.3); 7.2694 (1.4); 7.2686 (1.5); 7.2678 (1.7); 7.2670 (2.0);7.2662 (2.3); 7.2653 (2.8); 7.2637 (4.3); 7.2596 (203.6); 7.2091 (1.0);7.1916 (0.9); 7.1841 (1.3); 7.1801 (5.1); 7.1770 (2.8); 7.1725 (3.2);7.1699 (3.0); 7.1658 (3.3); 7.1638 (2.8); 7.1614 (2.1); 7.1589 (2.0);7.1557 (3.8); 7.1517 (0.7); 7.1040 (0.7); 7.0968 (5.4); 7.0913 (1.6);7.0830 (0.8); 7.0798 (1.7); 7.0757 (7.5); 7.0704 (1.8); 7.0672 (0.7);7.0589 (1.5); 7.0534 (4.3); 6.9956 (1.4); 5.9912 (0.5); 5.3318 (1.2);5.3142 (4.6); 5.2967 (4.6); 5.2791 (1.2); 2.0049 (3.0); 1.7453 (16.0);1.7277 (15.8); 1.6955 (0.7); 1.6782 (0.7); 0.0080 (3.0); −0.0002(104.2); −0.0085 (3.0); −0.0506 (0.5) I-117: ¹H-NMR(400.0 MHz, d₆-DMSO):δ = 8.3124 (4.8); 7.5517 (3.9); 7.5369 (4.1); 7.5167 (2.9); 7.4667(2.2); 7.4465 (5.1); 7.4300 (4.8); 7.4097 (3.9); 7.3783 (3.4); 7.2860(4.9); 7.2666 (6.2); 7.2277 (4.8); 7.2073 (4.6); 7.1880 (4.0); 7.1688(2.9); 7.1639 (3.9); 7.0516 (4.4); 7.0348 (3.8); 5.0096 (2.9); 4.9925(3.1); 3.3146 (10.8); 2.6694 (2.9); 2.5094 (189.0); 2.5049 (389.4);2.5003 (530.0); 2.4957 (370.7); 2.4912 (170.7); 2.3273 (3.4); 1.9874(2.3); 1.5249 (16.0); 1.5076 (16.0); −0.0002 (28.3) I-118: ¹H-NMR(400.0MHz, CDCl3): δ = 7.5182 (1.0); 7.3750 (0.7); 7.3612 (0.8); 7.3553 (1.2);7.3407 (1.3); 7.3358 (1.0); 7.3211 (1.0); 7.2763 (0.6); 7.2755 (0.6);7.2747 (0.6); 7.2739 (0.6); 7.2731 (0.7); 7.2723 (0.7); 7.2715 (0.8);7.2707 (0.8); 7.2699 (0.9); 7.2691 (1.0); 7.2683 (1.2); 7.2675 (1.3);7.2667 (1.5); 7.2659 (1.7); 7.2651 (2.0); 7.2643 (2.4); 7.2635 (3.1);7.2593 (181.8); 7.1213 (2.7); 7.1159 (1.5); 7.1095 (2.6); 7.1040 (1.7);7.1016 (1.6); 7.0986 (4.2); 7.0952 (1.6); 7.0926 (2.2); 7.0865 (3.3);7.0805 (0.7); 7.0781 (1.0); 7.0740 (0.7); 7.0715 (0.6); 7.0396 (1.3);7.0370 (1.6); 7.0358 (1.8); 7.0332 (1.6); 7.0205 (1.1); 7.0167 (1.8);7.0141 (1.6); 7.0089 (1.2); 7.0026 (1.1); 6.9993 (0.8); 6.9953 (1.2);6.9927 (0.6); 6.9844 (3.7); 6.9789 (1.6); 6.9762 (1.0); 6.9725 (0.6);6.9672 (1.0); 6.9641 (3.6); 6.9616 (2.8); 6.9584 (1.1); 6.9470 (0.8);6.9413 (2.4); 4.9737 (16.0); 2.9626 (1.2); 2.8902 (1.1); 1.8551 (0.6);0.0079 (2.3); 0.0064 (0.6); 0.0055 (0.7); 0.0047 (0.8); −0.0002 (76.6);−0.0059 (1.2); −0.0067 (1.0); −0.0085 (2.4) I-119: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.5182 (0.9); 7.3707 (0.7); 7.3558 (1.1); 7.3498 (1.7);7.3354 (1.7); 7.3296 (1.3); 7.3154 (1.4); 7.2659 (1.8); 7.2592 (171.5);7.1462 (0.7); 7.1374 (2.9); 7.1319 (1.1); 7.1256 (3.4); 7.1199 (2.7);7.1145 (4.8); 7.1108 (1.8); 7.1028 (4.3); 7.0986 (1.8); 7.0957 (1.8);7.0897 (2.0); 7.0775 (0.8); 7.0751 (0.8); 7.0710 (0.8); 7.0685 (0.9);7.0460 (1.7); 7.0422 (2.6); 7.0397 (2.2); 7.0244 (4.7); 7.0207 (3.3);7.0029 (1.8); 6.9971 (5.6); 6.9918 (1.9); 6.9854 (0.8); 6.9769 (4.8);6.9711 (1.5); 6.9599 (1.0); 6.9541 (3.0); 4.9821 (16.0); 4.9283 (1.0);3.8129 (1.9); 2.0446 (0.8); 1.2585 (0.6); 0.0079 (1.9); −0.0002 (69.8);−0.0085 (2.2) I-120: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5184 (0.5); 7.3704(0.6); 7.3555 (0.8); 7.3524 (0.6); 7.3496 (1.2); 7.3351 (1.3); 7.3305(0.9); 7.3154 (1.0); 7.2709 (0.5); 7.2693 (0.6); 7.2685 (0.7); 7.2677(0.8); 7.2669 (0.8); 7.2661 (1.0); 7.2652 (1.2); 7.2644 (1.4); 7.2636(1.8); 7.2595 (92.6); 7.2530 (0.6); 7.1479 (2.5); 7.1421 (1.0); 7.1360(2.8); 7.1306 (1.6); 7.1250 (3.6); 7.1190 (1.2); 7.1132 (4.1); 7.1095(0.9); 7.1070 (0.9); 7.1048 (0.5); 7.0948 (1.2); 7.0920 (1.2); 7.0882(0.9); 7.0858 (1.4); 7.0737 (0.6); 7.0712 (0.6); 7.0671 (0.6); 7.0647(0.7); 7.0440 (1.4); 7.0414 (1.6); 7.0401 (2.0); 7.0376 (1.7); 7.0219(3.5); 7.0185 (2.2); 7.0135 (1.1); 7.0050 (3.6); 6.9995 (2.0); 6.9956(1.6); 6.9933 (1.5); 6.9880 (1.3); 6.9848 (3.9); 6.9822 (2.9); 6.9790(1.2); 6.9677 (0.9); 6.9619 (2.5); 4.9819 (16.0); 3.7571 (0.5); 2.9661(1.9); 2.8941 (1.7); 2.8926 (1.8); 1.8576 (0.6); 1.4319 (0.8); 0.0080(1.2); 0.0048 (0.5); 0.0040 (0.6); −0.0002 (39.1); −0.0084 (1.1) I-121:¹H-NMR(400.0 MHz, CDCl3): δ = 7.5185 (1.1); 7.4037 (0.6); 7.3890 (1.0);7.3857 (0.7); 7.3829 (1.3); 7.3690 (1.4); 7.3639 (1.0); 7.3492 (1.2);7.2597 (198.1); 7.1909 (0.8); 7.1884 (0.8); 7.1842 (0.8); 7.1819 (0.9);7.1697 (1.4); 7.1670 (1.3); 7.1634 (1.2); 7.1608 (1.5); 7.1485 (0.9);7.1393 (3.3); 7.1335 (1.1); 7.1275 (3.0); 7.1218 (2.0); 7.1162 (4.0);7.1104 (1.2); 7.1045 (3.9); 7.0962 (0.6); 7.0783 (1.5); 7.0744 (2.2);7.0719 (2.0); 7.0561 (3.7); 7.0529 (2.4); 7.0350 (1.3); 7.0292 (1.2);7.0253 (1.3); 7.0171 (3.9); 7.0112 (1.2); 7.0055 (0.6); 6.9972 (4.2);6.9942 (3.3); 6.9914 (1.4); 6.9800 (1.0); 6.9743 (2.7); 5.0798 (16.0);4.9644 (1.4); 3.8227 (0.7); 3.0213 (0.8); 2.9521 (0.7); 2.1027 (3.4);2.0449 (1.1); 1.2587 (0.8); 0.0080 (2.4); −0.0002 (84.0); −0.0085 (2.3)I-122: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4991 (0.7); 7.4812 (0.6); 7.4744(1.4); 7.4595 (0.8); 7.4560 (1.4); 7.4524 (0.7); 7.4304 (1.6); 7.4269(0.8); 7.4154 (1.4); 7.4115 (2.9); 7.3980 (0.6); 7.3936 (1.4); 7.3903(0.9); 7.3661 (0.6); 7.3634 (0.6); 7.3458 (0.6); 7.3229 (2.4); 7.3199(2.8); 7.3161 (1.4); 7.3076 (0.7); 7.3025 (2.3); 7.2987 (1.6); 7.2602(14.6); 7.2272 (0.6); 7.2119 (0.6); 7.2066 (1.3); 7.1913 (1.2); 7.1860(0.8); 7.1708 (0.7); 7.0015 (0.5); 6.9993 (0.5); 6.9870 (0.8); 6.9850(0.8); 6.9807 (0.9); 6.9787 (0.8); 6.9580 (0.6); 6.9356 (0.9); 6.9301(1.3); 6.9246 (0.7); 6.9120 (0.7); 6.9066 (1.1); 6.9008 (0.6); 6.8438(0.9); 6.8401 (0.8); 6.8235 (0.8); 6.8198 (0.7); 5.2972 (0.8); 5.0502(2.0); 5.0368 (8.8); 3.8448 (3.7); 3.8317 (16.0); 3.8173 (0.8); −0.0002(6.2) I-123: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3660 (0.7); 7.3638 (0.5);7.3507 (1.0); 7.3480 (0.8); 7.3451 (1.4); 7.3307 (1.6); 7.3259 (1.1);7.3108 (1.2); 7.2917 (0.8); 7.2771 (0.9); 7.2719 (1.7); 7.2586 (40.0);7.2524 (1.8); 7.2375 (1.2); 7.1246 (1.9); 7.1234 (1.9); 7.1137 (0.9);7.1112 (1.0); 7.1047 (2.3); 7.0926 (1.3); 7.0898 (1.4); 7.0862 (1.2);7.0837 (1.6); 7.0714 (0.7); 7.0690 (0.8); 7.0650 (0.9); 7.0625 (1.0);7.0585 (3.1); 7.0528 (2.2); 7.0467 (3.3); 7.0412 (2.1); 7.0356 (6.7);7.0322 (3.1); 7.0297 (2.8); 7.0238 (5.7); 7.0166 (4.8); 7.0131 (3.0);7.0020 (1.5); 6.9950 (2.4); 6.9910 (1.6); 6.9846 (1.2); 6.9774 (1.4);6.9694 (4.3); 6.9635 (1.2); 6.9574 (0.7); 6.9491 (4.5); 6.9434 (1.3);6.9321 (0.9); 6.9264 (2.4); 5.2973 (1.9); 5.2422 (11.0); 4.9719 (16.0);4.9277 (0.5); 3.8122 (0.9); 2.2706 (0.9); 1.5396 (2.0); 1.4318 (8.6);−0.0002 (16.0); −0.0085 (0.5) I-124: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3669 (2.2); 7.3602 (2.0); 7.3517 (3.5); 7.3486 (3.3); 7.3419 (4.1);7.3327 (2.3); 7.3272 (2.8); 7.3232 (2.0); 7.3178 (9.4); 7.3115 (7.0);7.3060 (2.6); 7.3009 (3.1); 7.2960 (0.7); 7.2924 (0.7); 7.2576 (39.0);7.1135 (0.8); 7.1111 (0.9); 7.1070 (0.9); 7.1047 (0.9); 7.0923 (1.3);7.0899 (1.5); 7.0858 (1.4); 7.0835 (1.5); 7.0712 (0.6); 7.0688 (0.7);7.0646 (0.7); 7.0624 (0.7); 7.0250 (3.1); 7.0206 (3.1); 7.0183 (2.2);7.0138 (2.8); 7.0085 (2.0); 7.0029 (6.1); 6.9991 (2.4); 6.9971 (1.8);6.9909 (5.5); 6.9840 (1.7); 6.9805 (1.2); 6.9673 (1.4); 6.9634 (1.4);6.9612 (1.4); 6.9568 (1.4); 6.9484 (4.4); 6.9424 (1.2); 6.9362 (0.7);6.9281 (4.7); 6.9224 (1.4); 6.9111 (0.9); 6.9053 (2.4); 5.2962 (1.1);5.2548 (13.0); 4.9502 (16.0); 4.5006 (0.5); 1.5392 (2.0); 1.4317 (3.7);0.0701 (2.0); −0.0002 (14.8) I-127: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5184(2.0); 7.4222 (1.1); 7.4142 (5.0); 7.4107 (5.3); 7.4046 (2.1); 7.4004(2.2); 7.3962 (3.4); 7.3873 (1.0); 7.3831 (1.2); 7.3774 (0.6); 7.3724(0.6); 7.3072 (3.7); 7.3029 (4.1); 7.2960 (1.6); 7.2932 (1.8); 7.2906(2.2); 7.2884 (2.3); 7.2829 (3.2); 7.2595 (362.7); 7.2239 (1.3); 7.2102(0.6); 7.1940 (0.8); 7.1888 (1.6); 7.1734 (1.4); 7.1681 (1.0); 7.1531(0.9); 6.9956 (2.1); 6.9611 (0.8); 6.9554 (1.4); 6.9497 (1.1); 6.9364(1.5); 6.9305 (1.8); 6.9257 (1.2); 6.9157 (1.5); 6.9134 (1.6); 6.9094(1.0); 6.8927 (0.9); 6.8886 (0.7); 6.8783 (1.3); 6.8582 (1.1); 6.8553(1.0); 5.0006 (16.0); 2.0444 (0.5); 1.5663 (1.1); 1.2587 (0.7); 0.1579(0.5); 0.0080 (4.5); −0.0002 (152.0); −0.0085 (5.7); −0.1495 (0.5)I-128: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5183 (0.7); 7.4275 (1.1); 7.4224(1.7); 7.4145 (6.5); 7.4109 (7.2); 7.4048 (3.1); 7.4006 (2.8); 7.3964(4.5); 7.3948 (4.0); 7.3876 (1.5); 7.3834 (1.7); 7.3775 (0.8); 7.3731(1.0); 7.3094 (0.8); 7.2911 (5.0); 7.2869 (5.6); 7.2818 (2.8); 7.2798(2.8); 7.2773 (2.7); 7.2744 (3.5); 7.2724 (3.8); 7.2669 (5.6); 7.2594(119.9); 7.1937 (1.2); 7.1782 (1.3); 7.1733 (2.3); 7.1579 (2.1); 7.1532(1.4); 7.1378 (1.2); 6.9954 (0.7); 6.9352 (1.0); 6.9299 (2.1); 6.9248(1.7); 6.9163 (1.4); 6.9140 (1.6); 6.9104 (1.6); 6.9053 (2.2); 6.9002(1.9); 6.8957 (2.3); 6.8933 (2.5); 6.8894 (1.5); 6.8870 (1.4); 6.8750(1.1); 6.8728 (1.2); 6.8687 (1.0); 6.8641 (2.1); 6.8617 (2.1); 6.8594(1.9); 6.8569 (1.6); 6.8436 (1.7); 6.8416 (1.7); 6.8389 (1.6); 4.9914(16.0); 2.0450 (0.8); 1.2586 (0.6); 0.0080 (1.6); −0.0002 (49.6);−0.0085 (2.2) I-129: ¹H-NMR(400.0 MHz, CDCl3): δ = 10.5842 (0.5); 7.9716(0.6); 7.9485 (0.7); 7.5190 (1.1); 7.5010 (1.3); 7.4975 (0.7); 7.4890(0.7); 7.4822 (3.1); 7.4764 (0.9); 7.4675 (1.3); 7.4640 (2.5); 7.4605(1.4); 7.4365 (2.6); 7.4332 (1.4); 7.4215 (2.3); 7.4177 (4.7); 7.4042(0.8); 7.3998 (2.4); 7.3965 (1.5); 7.3672 (1.1); 7.3496 (1.2); 7.3325(0.9); 7.3274 (3.8); 7.3245 (4.7); 7.3122 (1.1); 7.3070 (3.7); 7.3032(2.6); 7.2600 (160.0); 7.2385 (0.9); 7.2235 (1.2); 7.2180 (1.9); 7.2103(1.0); 7.2029 (1.9); 7.1974 (1.2); 7.1821 (1.2); 7.0335 (0.6); 7.0275(0.7); 7.0177 (0.8); 7.0155 (0.8); 7.0092 (0.8); 6.9960 (2.0); 6.9906(1.4); 6.9886 (1.4); 6.9761 (0.7); 6.9741 (0.7); 6.9701 (0.8); 6.9419(1.2); 6.9366 (1.9); 6.9309 (1.1); 6.9184 (1.2); 6.9131 (1.8); 6.9073(1.0); 6.8647 (1.5); 6.8612 (1.4); 6.8445 (1.2); 6.8410 (1.2); 6.0463(0.5); 5.1063 (4.1); 5.0941 (16.0); 5.0017 (0.7); 4.9442 (1.0); 4.8496(0.5); 3.7744 (0.7); 3.7639 (0.7); 3.7577 (1.8); 3.7411 (0.7); 3.6087(0.6); 1.8751 (0.9); 1.8673 (0.8); 1.8586 (2.3); 1.8499 (0.8); 1.8420(0.8); 0.0080 (2.2); −0.0002 (66.7); −0.0085 (2.1) I-130: ¹H-NMR(400.0MHz, CDCl3): δ = 7.3316 (3.7); 7.3226 (5.0); 7.3158 (6.2); 7.3046 (2.9);7.2955 (2.6); 7.2876 (1.4); 7.2825 (2.3); 7.2606 (8.2); 7.1666 (2.4);7.1578 (2.5); 7.1536 (2.0); 7.1488 (2.0); 7.1426 (1.9); 7.0919 (2.2);7.0705 (3.8); 7.0489 (1.8); 5.2969 (2.6); 5.2622 (0.6); 5.2448 (1.8);5.2273 (1.8); 5.2099 (0.6); 3.7819 (16.0); 1.6914 (7.4); 1.6739 (7.3);1.5622 (0.5); −0.0002 (3.0) I-131: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5184(1.1); 7.3920 (0.9); 7.3878 (1.1); 7.3730 (1.7); 7.3684 (2.4); 7.3550(1.4); 7.3494 (2.1); 7.3440 (1.1); 7.3363 (1.2); 7.3283 (1.0); 7.3234(0.8); 7.3159 (0.9); 7.3091 (1.0); 7.2595 (207.3); 7.2122 (1.6); 7.1945(2.0); 7.1731 (0.9); 7.1416 (1.9); 7.1369 (1.2); 7.1202 (2.2); 7.1095(1.3); 7.0999 (1.6); 7.0957 (2.6); 7.0908 (1.3); 7.0750 (1.2); 7.0605(1.3); 7.0571 (1.1); 7.0357 (2.0); 7.0145 (1.2); 7.0062 (1.0); 7.0023(1.1); 6.9956 (2.3); 6.9916 (1.2); 6.9796 (0.8); 6.9708 (0.8); 4.8919(16.0); 4.2949 (2.0); 4.2771 (6.3); 4.2592 (6.5); 4.2414 (2.3); 4.2306(0.9); 4.0988 (0.5); 1.5367 (14.5); 1.3058 (7.5); 1.2879 (14.9); 1.2701(7.8); 1.2543 (1.8); 0.0080 (2.5); −0.0002 (74.4); −0.0083 (3.0) I-132:¹H-NMR(400.0 MHz, CDCl3): δ = 7.2775 (1.0); 7.2722 (0.9); 7.2593 (47.0);7.2421 (1.1); 7.2364 (1.2); 7.2223 (0.7); 7.1101 (0.9); 7.1062 (1.3);7.0888 (0.9); 7.0858 (0.7); 7.0730 (0.9); 7.0513 (1.4); 7.0294 (0.7);5.2640 (0.8); 5.2466 (0.8); 3.7878 (7.6); 1.6968 (3.2); 1.6793 (3.2);1.5355 (16.0); 0.0079 (0.6); −0.0002 (17.6); −0.0084 (0.7) I-133:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3813 (0.8); 7.3769 (1.0); 7.3621 (1.4);7.3577 (2.0); 7.3480 (0.7); 7.3433 (1.4); 7.3392 (1.9); 7.3287 (1.2);7.3242 (0.7); 7.3204 (1.0); 7.3160 (0.7); 7.3083 (0.8); 7.3039 (0.8);7.2597 (38.3); 7.2558 (2.1); 7.2066 (0.9); 7.2031 (1.2); 7.1873 (1.5);7.1856 (1.4); 7.1837 (1.4); 7.1681 (0.7); 7.1645 (0.6); 7.1485 (0.9);7.1432 (1.1); 7.1377 (0.9); 7.1298 (1.0); 7.1244 (1.1); 7.1214 (1.1);7.1164 (2.3); 7.1127 (1.0); 7.1027 (0.9); 7.0968 (1.7); 7.0917 (1.4);7.0712 (1.1); 7.0532 (1.1); 7.0498 (1.0); 7.0325 (1.0); 7.0285 (1.7);7.0247 (1.1); 7.0096 (1.0); 7.0066 (1.5); 7.0043 (1.6); 6.9991 (1.0);6.9955 (1.2); 6.9902 (0.8); 6.9847 (0.7); 6.9793 (0.6); 6.9740 (0.6);6.9688 (0.5); 4.8903 (14.9); 4.8862 (1.6); 4.2919 (1.9); 4.2741 (6.0);4.2703 (0.7); 4.2563 (6.0); 4.2525 (0.6); 4.2385 (2.0); 1.5438 (13.1);1.5400 (0.7); 1.3038 (8.0); 1.3005 (1.0); 1.2860 (16.0); 1.2826 (1.8);1.2682 (9.1); 1.2647 (2.6); 0.8987 (1.1); 0.8817 (4.0); 0.8640 (1.5);−0.0002 (13.9); −0.0040 (0.8) I-134: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3790 (0.5); 7.3637 (1.0); 7.3572 (1.0); 7.3484 (0.6); 7.3423 (2.0);7.3361 (0.7); 7.3268 (1.0); 7.3209 (1.2); 7.3057 (0.6); 7.2600 (30.0);7.1873 (0.9); 7.1820 (1.0); 7.1686 (1.0); 7.1608 (1.2); 7.1553 (1.1);7.1505 (1.0); 7.1418 (1.0); 7.1367 (1.1); 7.1293 (1.7); 7.1257 (1.0);7.1091 (1.3); 7.1044 (1.6); 7.0843 (1.2); 7.0504 (0.8); 7.0459 (1.1);7.0400 (1.2); 7.0352 (1.2); 7.0311 (0.9); 7.0251 (0.8); 7.0191 (0.7);7.0145 (0.7); 6.9554 (3.0); 6.9370 (4.0); 6.9340 (4.0); 6.9156 (2.6);4.8743 (16.0); 4.2811 (2.0); 4.2632 (6.3); 4.2454 (6.4); 4.2275 (2.1);1.5445 (11.0); 1.3037 (0.7); 1.2900 (7.9); 1.2722 (16.0); 1.2543 (7.9);0.8982 (1.2); 0.8815 (3.8); 0.8638 (1.6); 0.0079 (0.5); −0.0002 (15.1);−0.0084 (0.7) I-135: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.2791 (1.0); 7.2736(0.6); 7.2654 (1.6); 7.2594 (33.1); 7.2495 (1.1); 7.2437 (1.4); 7.2367(1.5); 7.2317 (0.7); 7.2215 (0.6); 7.2176 (1.4); 7.2007 (0.8); 7.1971(0.5); 7.1832 (0.7); 7.0837 (1.3); 7.0797 (2.0); 7.0778 (1.7); 7.0665(0.7); 7.0595 (1.4); 7.0556 (2.1); 7.0508 (0.5); 7.0338 (1.0); 3.7461(10.0); 2.9553 (0.6); 2.8833 (0.5); 2.7723 (1.4); 1.7553 (16.0); 1.5440(1.2); 0.0080 (0.6); −0.0002 (16.8); −0.0084 (0.7) I-136: ¹H-NMR(400.0MHz, CDCl3): δ = 7.3977 (0.9); 7.3935 (1.1); 7.3785 (1.7); 7.3744 (2.1);7.3663 (0.7); 7.3591 (1.5); 7.3552 (1.8); 7.3518 (1.3); 7.3472 (0.9);7.3392 (1.1); 7.3336 (1.0); 7.3311 (1.0); 7.3267 (0.8); 7.3188 (0.9);7.3144 (0.7); 7.2597 (43.0); 7.2129 (1.3); 7.1935 (1.9); 7.1759 (0.8);7.1506 (1.0); 7.1450 (1.7); 7.1319 (1.1); 7.1237 (2.8); 7.1190 (1.8);7.1033 (1.8); 7.0993 (2.4); 7.0782 (1.1); 7.0597 (1.3); 7.0565 (1.2);7.0388 (1.3); 7.0351 (2.0); 7.0314 (1.3); 7.0139 (1.9); 7.0105 (2.0);7.0037 (1.2); 6.9996 (1.2); 6.9950 (1.0); 6.9886 (0.8); 6.9824 (0.8);6.9780 (0.7); 6.9733 (0.5); 4.9654 (16.0); 4.1318 (1.2); 4.1140 (1.2);2.0453 (5.5); 1.4318 (0.7); 1.2764 (1.5); 1.2585 (2.9); 1.2407 (1.4);0.0079 (0.8); −0.0002 (22.6); −0.0083 (1.0) I-137: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3871 (0.5); 7.3718 (1.0); 7.3656 (0.9); 7.3565 (0.6);7.3504 (1.9); 7.3442 (0.6); 7.3351 (0.9); 7.3290 (1.1); 7.3137 (0.6);7.2607 (30.4); 7.1884 (0.9); 7.1831 (0.9); 7.1696 (0.9); 7.1643 (1.1);7.1618 (1.1); 7.1562 (1.6); 7.1430 (0.9); 7.1349 (1.6); 7.1311 (0.9);7.1147 (1.3); 7.1099 (1.4); 7.0900 (1.1); 7.0533 (0.8); 7.0497 (0.9);7.0428 (1.0); 7.0393 (1.0); 7.0341 (0.8); 7.0284 (0.6); 7.0232 (0.6);7.0179 (0.6); 6.9709 (0.5); 6.9655 (1.2); 6.9626 (2.8); 6.9442 (3.7);6.9411 (3.5); 6.9360 (0.6); 6.9229 (2.4); 6.9198 (1.0); 5.2985 (4.2);4.9432 (16.0); 3.7819 (0.8); 3.7783 (3.0); 3.7763 (2.0); 3.7720 (1.9);3.7699 (1.6); 3.7679 (2.5); 3.7617 (7.5); 3.7556 (2.6); 3.7513 (1.9);3.7470 (2.0); 3.7450 (3.1); 3.7415 (0.7); 1.8763 (3.0); 1.8685 (2.8);1.8643 (2.0); 1.8597 (9.0); 1.8549 (2.1); 1.8508 (2.8); 1.8430 (3.0);1.8391 (0.7); 1.4319 (0.8); −0.0002 (17.0); −0.0085 (0.7) I-138:¹H-NMR(400.0 MHz, CDCl3): δ = 7.5182 (1.6); 7.3446 (0.8); 7.2593(301.4); 7.2485 (9.6); 7.2465 (9.6); 7.2399 (4.8); 7.2360 (6.9); 7.2315(7.1); 7.2273 (14.9); 7.2187 (8.3); 7.2140 (8.9); 7.2085 (2.4); 7.2024(3.5); 7.1831 (1.1); 7.1687 (0.6); 7.1120 (6.8); 7.1079 (8.6); 7.1022(2.5); 7.0955 (3.6); 7.0910 (6.9); 7.0877 (5.7); 7.0612 (6.7); 7.0558(2.4); 7.0394 (10.5); 7.0231 (2.0); 7.0177 (5.3); 6.9952 (1.6); 5.2993(1.2); 5.2821 (4.4); 5.2646 (4.5); 5.2472 (1.2); 3.8179 (1.1); 1.7194(16.0); 1.7020 (16.0); 1.4318 (0.7); 1.2557 (1.0); 0.1462 (0.5); 0.0080(5.0); −0.0002 (159.4); −0.0084 (5.4); −0.1498 (0.6) I-139: ¹H-NMR(400.0MHz, CDCl3): δ = 19.9731 (0.8); 7.5183 (2.5); 7.3101 (0.9); 7.2930(1.7); 7.2879 (2.5); 7.2711 (13.4); 7.2594 (475.1); 7.2526 (17.5);7.2436 (7.6); 7.2360 (6.9); 7.2274 (3.8); 7.2094 (2.5); 7.1355 (6.0);7.1314 (7.6); 7.1145 (6.1); 7.1113 (5.1); 7.0781 (6.1); 7.0564 (9.6);7.0345 (4.8); 6.9954 (2.5); 5.3315 (1.2); 5.3139 (4.4); 5.2965 (4.5);5.2788 (1.3); 1.7459 (15.8); 1.7284 (16.0); 1.2562 (0.8); 0.1458 (0.9);0.0079 (8.1); −0.0002 (246.6); −0.0084 (8.8); −0.0499 (0.9); −0.1499(0.9) I-140: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5189 (0.8); 7.2600 (132.6);7.2336 (4.5); 7.2164 (2.5); 7.1101 (2.3); 7.0932 (2.1); 7.0732 (1.7);7.0520 (2.8); 7.0304 (1.4); 6.9960 (0.8); 2.0043 (0.9); 1.7788 (16.0);1.2553 (0.7); 0.0079 (3.3); −0.0002 (78.0); −0.0084 (4.2) I-141:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3390 (0.7); 7.3319 (2.8); 7.3229 (3.6);7.3156 (4.9); 7.3046 (2.2); 7.2997 (1.2); 7.2952 (2.2); 7.2877 (1.0);7.2823 (2.0); 7.2602 (10.9); 7.1667 (1.9); 7.1576 (1.9); 7.1533 (1.4);7.1487 (1.5); 7.1459 (1.1); 7.1423 (1.6); 7.0922 (2.0); 7.0869 (0.7);7.0707 (3.2); 7.0661 (0.9); 7.0542 (0.6); 7.0490 (1.6); 5.2973 (1.3);5.2446 (1.7); 5.2271 (1.7); 5.2097 (0.5); 3.7821 (16.0); 1.6915 (6.8);1.6740 (6.8); 1.5553 (0.5); −0.0002 (4.2) I-146: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3732 (1.0); 7.3668 (0.8); 7.3580 (0.6); 7.3518 (2.0);7.3455 (0.7); 7.3363 (0.9); 7.3304 (1.2); 7.3151 (0.6); 7.2650 (0.5);7.2592 (51.0); 7.1808 (0.8); 7.1756 (0.9); 7.1622 (0.9); 7.1545 (1.7);7.1488 (1.1); 7.1347 (1.8); 7.1300 (1.8); 7.1135 (1.2); 7.1087 (1.4);7.0887 (1.1); 7.0460 (0.7); 7.0410 (0.8); 7.0354 (1.0); 7.0318 (1.0);7.0266 (0.8); 7.0209 (0.7); 7.0157 (0.6); 7.0104 (0.6); 6.9772 (0.9);6.9730 (0.6); 6.9673 (1.1); 6.9644 (2.9); 6.9513 (0.6); 6.9460 (3.7);6.9429 (3.7); 6.9247 (2.6); 6.9216 (1.1); 6.9164 (0.5); 5.9521 (0.6);5.9380 (1.2); 5.9260 (0.7); 5.9239 (0.7); 5.9118 (1.3); 5.9092 (0.8);5.8976 (0.7); 5.8950 (1.4); 5.8829 (0.8); 5.8809 (0.8); 5.8688 (1.4);5.8547 (0.7); 5.3471 (0.7); 5.3433 (2.0); 5.3396 (2.1); 5.3358 (0.9);5.3042 (0.6); 5.3003 (1.7); 5.2966 (1.9); 5.2928 (0.8); 5.2365 (0.8);5.2334 (2.1); 5.2301 (2.2); 5.2269 (0.9); 5.2104 (0.8); 5.2072 (2.0);5.2039 (2.1); 5.2007 (0.9); 5.0015 (0.7); 4.9177 (15.3); 4.7050 (2.4);4.7015 (4.0); 4.6981 (2.7); 4.6909 (2.6); 4.6874 (4.0); 4.6839 (2.7);2.2705 (1.7); 1.5390 (4.2); 1.4319 (16.0); 1.2559 (0.9); 0.0080 (0.5);−0.0002 (19.1); −0.0085 (0.9) I-149: ¹H-NMR(400.0 MHz, CDCl3): δ =7.4454 (0.5); 7.4300 (1.1); 7.4238 (1.0); 7.4146 (0.6); 7.4085 (2.0);7.4024 (0.7); 7.3931 (1.0); 7.3869 (1.2); 7.3716 (0.6); 7.2596 (76.5);7.2239 (1.0); 7.2190 (0.9); 7.2057 (0.9); 7.1994 (1.3); 7.1931 (0.9);7.1770 (1.3); 7.1559 (1.5); 7.1525 (1.0); 7.1362 (1.4); 7.1312 (1.4);7.1119 (1.2); 7.0784 (1.0); 7.0726 (1.0); 7.0678 (1.0); 7.0569 (0.7);7.0513 (0.6); 7.0467 (0.6); 6.9957 (0.5); 6.9870 (1.5); 6.9835 (2.6);6.9654 (3.8); 6.9619 (3.8); 6.9438 (2.3); 6.9401 (1.3); 5.9436 (0.5);5.9293 (1.1); 5.9174 (0.7); 5.9151 (0.6); 5.9032 (1.3); 5.9009 (0.8);5.8887 (0.8); 5.8863 (1.4); 5.8744 (0.8); 5.8721 (0.8); 5.8602 (1.4);5.8459 (0.7); 5.3474 (0.8); 5.3437 (2.2); 5.3400 (2.2); 5.3363 (0.9);5.3044 (0.7); 5.3007 (1.9); 5.2971 (2.0); 5.2933 (0.8); 5.2412 (0.9);5.2382 (2.3); 5.2351 (2.2); 5.2320 (0.9); 5.2151 (0.9); 5.2121 (2.1);5.2090 (2.1); 5.2059 (0.8); 5.0047 (16.0); 4.7072 (2.9); 4.7038 (4.7);4.7004 (2.9); 4.6929 (3.0); 4.6895 (4.6); 4.6861 (2.8); 1.5355 (14.9);1.4319 (1.3); 0.0078 (0.8); −0.0002 (27.7); −0.0086 (1.2) I-150:¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.6062 (2.4); 7.5988 (2.4); 7.5721(2.3); 7.5649 (2.4); 7.5109 (1.6); 7.4967 (1.1); 7.4828 (3.8); 7.4756(1.7); 7.4686 (2.2); 7.4555 (3.2); 7.4465 (3.0); 7.4401 (2.1); 7.4183(1.8); 7.4054 (4.2); 7.4027 (4.1); 7.3983 (2.8); 7.3769 (1.9); 7.3732(2.3); 7.2294 (1.0); 7.2230 (1.0); 7.2016 (1.8); 7.1950 (1.7); 7.1753(0.8); 7.1669 (0.8); 4.9336 (12.6); 4.2054 (2.2); 4.1817 (6.8); 4.1580(6.9); 4.1344 (2.2); 3.3214 (19.8); 2.5141 (10.6); 2.5085 (19.2); 2.5026(24.1); 2.4968 (16.6); 1.9894 (0.8); 1.2348 (0.5); 1.2119 (7.8); 1.1883(16.0); 1.1750 (1.2); 1.1646 (7.3); 1.1514 (0.4); 0.0107 (0.8); 0.0000(15.2); −0.0110 (0.6) I-151: ¹H-NMR(300.3 MHz, d₆-DMSO): δ = 7.6216(4.0); 7.5923 (3.8); 7.5816 (3.3); 7.5246 (2.0); 7.4965 (4.6); 7.4691(3.5); 7.4334 (4.1); 7.4117 (13.2); 7.3817 (3.0); 4.9452 (15.7); 4.2088(2.5); 4.1852 (7.7); 4.1615 (7.8); 4.1379 (2.6); 3.3717 (41.8); 3.3661(39.4); 2.5111 (5.1); 2.0832 (0.4); 1.2304 (1.2); 1.2138 (8.0); 1.1902(16.0); 1.1666 (7.7); −0.0001 (0.4) I-152: ¹H-NMR(300.1 MHz, d₆-DMSO): δ= 7.7620 (4.8); 7.7572 (4.5); 7.6027 (2.6); 7.5973 (2.6); 7.5672 (4.0);7.5385 (8.3); 7.5283 (5.2); 7.5061 (0.7); 7.4997 (0.8); 7.4262 (0.9);7.3983 (3.7); 7.3806 (8.3); 7.3586 (0.7); 7.3524 (0.6); 4.9164 (13.0);4.1929 (2.3); 4.1692 (7.0); 4.1455 (7.1); 4.1219 (2.4); 3.3282 (74.2);2.5100 (10.8); 2.5043 (13.2); 2.4986 (9.3); 1.2333 (1.1); 1.2086 (7.8);1.1849 (16.0); 1.1612 (7.4); 0.0001 (5.4) I-153: ¹H-NMR(300.1 MHz,d₆-DMSO): δ = 7.7512 (6.5); 7.7478 (6.6); 7.5704 (1.7); 7.5419 (8.8);7.5332 (7.4); 7.5040 (1.5); 7.4986 (1.5); 7.4798 (1.4); 7.4518 (2.9);7.4287 (3.3); 7.4230 (3.4); 7.4018 (2.1); 7.3823 (3.1); 7.3547 (1.7);7.3481 (1.7); 7.2075 (1.7); 7.2021 (1.7); 7.1796 (3.0); 7.1520 (1.6);4.9238 (15.8); 4.1992 (2.6); 4.1757 (7.6); 4.1521 (7.8); 4.1286 (2.8);3.3512 (38.7); 2.5127 (4.4); 2.0834 (0.4); 1.2335 (1.7); 1.2137 (8.4);1.1901 (16.0); 1.1665 (8.0); 0.0003 (0.6) I-154: ¹H-NMR(300.1 MHz,d₆-DMSO): δ = 7.7772 (5.7); 7.7711 (5.5); 7.6052 (2.7); 7.5981 (2.7);7.5709 (2.7); 7.5643 (2.8); 7.5520 (1.9); 7.5455 (1.6); 7.5242 (4.8);7.5177 (4.6); 7.4951 (6.6); 7.4671 (2.8); 7.4343 (3.7); 7.4081 (3.4);7.3831 (3.7); 7.3772 (3.2); 7.3539 (1.5); 7.3481 (1.4); 4.9380 (13.6);4.2073 (2.3); 4.1836 (6.9); 4.1599 (7.0); 4.1363 (2.3); 3.3233 (22.0);2.5089 (14.2); 2.5034 (17.3); 2.4980 (12.4); 1.2328 (0.8); 1.2144 (7.9);1.1907 (16.0); 1.1671 (7.5); 0.0001 (7.2) I-155: ¹H-NMR(3OO.1 MHz,d₆-DMSO): δ = 7.6142 (2.7); 7.6058 (2.8); 7.5957 (2.9); 7.5878 (3.5);7.5855 (3.4); 7.5763 (2.8); 7.5614 (2.9); 7.5549 (4.2); 7.5346 (2.2);7.5262 (2.5); 7.5060 (2.3); 7.4557 (1.6); 7.4274 (3.5); 7.4013 (3.4);7.3766 (3.4); 7.3695 (3.1); 7.3604 (1.9); 7.3514 (2.0); 7.3395 (1.7);7.3322 (2.7); 7.3236 (2.3); 7.3038 (1.2); 7.2952 (1.0); 4.9360 (13.0);4.2077 (2.2); 4.1840 (6.8); 4.1604 (6.9); 4.1367 (2.3); 3.3199 (10.7);2.5089 (10.6); 2.5031 (13.2); 2.4973 (9.0); 2.0757 (2.8); 1.2151 (7.8);1.1915 (16.0); 1.1678 (7.4); −0.0001 (7.8); −0.0111 (0.3) I-156:¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.5759 (3.7); 7.5497 (6.4); 7.5414(3.2); 7.5227 (2.9); 7.4206 (2.8); 7.4169 (2.6); 7.3919 (2.2); 7.3874(2.2); 7.3776 (2.5); 7.3699 (1.5); 7.3586 (3.3); 7.3478 (5.6); 7.3370(2.5); 7.3295 (5.0); 7.3073 (5.2); 7.2778 (6.9); 7.2482 (2.4); 4.9203(14.1); 4.2024 (2.3); 4.1788 (7.1); 4.1551 (7.2); 4.1315 (2.4); 3.3288(66.3); 2.5094 (9.8); 2.5039 (12.1); 2.4984 (8.8); 1.2341 (1.6); 1.2108(8.0); 1.1872 (16.0); 1.1635 (7.6); 0.0001 (2.4) I-157: ¹H-NMR(300.1MHz, d₆-DMSO): δ = 7.5937 (2.5); 7.5859 (3.2); 7.5593 (3.6); 7.5544(5.7); 7.5258 (8.1); 7.5191 (2.6); 7.5030 (3.0); 7.4968 (8.3); 7.4889(1.3); 7.4313 (2.3); 7.4278 (2.4); 7.4238 (2.2); 7.4026 (1.6); 7.3991(1.7); 7.3952 (1.5); 7.3320 (8.2); 7.3256 (2.7); 7.3096 (2.6); 7.3034(6.1); 4.9243 (12.8); 4.2026 (2.2); 4.1790 (6.9); 4.1553 (7.0); 4.1316(2.3); 3.3336 (64.1); 2.5107 (6.4); 2.5049 (8.0); 2.4992 (5.6); 2.0768(1.4); 1.2340 (0.7); 1.2105 (7.7); 1.1868 (16.0); 1.1631 (7.4); 0.0000(1.3) I-158: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.7502 (5.8); 7.7429 (5.9);7.6476 (3.9); 7.6192 (6.5); 7.5476 (4.1); 7.5401 (3.7); 7.5191 (2.5);7.5117 (2.3); 7.3687 (2.8); 7.3618 (1.9); 7.3499 (4.0); 7.3394 (6.0);7.3212 (5.2); 7.2903 (5.3); 7.2609 (7.3); 7.2315 (2.7); 5.0201 (0.4);4.9040 (14.6); 4.1908 (2.5); 4.1672 (7.3); 4.1435 (7.5); 4.1199 (2.7);4.0964 (0.3); 3.3330 (31.8); 2.5116 (6.2); 2.5066 (7.2); 1.2335 (1.6);1.2083 (8.2); 1.1847 (16.0); 1.1611 (7.8); 1.1294 (0.4); 0.0003 (1.3)I-159: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.7576 (5.5); 7.7502 (5.6);7.6480 (3.6); 7.6196 (6.3); 7.5537 (4.0); 7.5461 (3.6); 7.5253 (2.5);7.5175 (2.9); 7.5070 (6.5); 7.5008 (2.6); 7.4845 (3.4); 7.4785 (8.5);7.3172 (8.5); 7.3108 (2.8); 7.2947 (2.8); 7.2887 (6.2); 4.9041 (12.8);4.1888 (2.2); 4.1652 (6.9); 4.1415 (7.0); 4.1178 (2.3); 3.6856 (0.3);3.3222 (13.8); 2.5099 (7.6); 2.5041 (9.3); 2.4984 (6.5); 2.0767 (0.4);1.2357 (0.6); 1.2062 (7.8); 1.1826 (16.0); 1.1589 (7.4); 0.0001 (4.6)I-160: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.6095 (2.5); 7.6034 (2.4);7.5767 (2.5); 7.5709 (2.5); 7.5538 (1.6); 7.5265 (3.3); 7.5010 (3.0);7.4685 (3.8); 7.4623 (3.2); 7.4406 (1.8); 7.4344 (1.6); 7.2690 (0.8);7.2384 (8.9); 7.2330 (8.4); 7.2134 (16.0); 7.1843 (0.5); 7.1651 (0.4);7.1563 (0.3); 7.1257 (0.3); 4.9655 (11.9); 4.2257 (2.2); 4.2020 (6.4);4.1784 (6.5); 4.1547 (2.2); 3.3449 (33.4); 2.5140 (3.1); 2.5086 (3.7);1.2300 (7.6); 1.2064 (14.3); 1.1827 (6.8); 0.0000 (0.5) I-161:¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.6310 (2.4); 7.6246 (2.5); 7.5980(2.4); 7.5920 (2.5); 7.5638 (1.5); 7.5363 (3.4); 7.5112 (3.2); 7.4849(4.2); 7.4785 (4.2); 7.4679 (6.9); 7.4607 (2.9); 7.4576 (2.6); 7.4504(2.5); 7.4455 (3.0); 7.4384 (8.2); 7.4284 (1.1); 7.2008 (1.2); 7.1908(8.0); 7.1837 (2.5); 7.1680 (2.6); 7.1613 (6.5); 7.1509 (0.7); 4.9686(11.8); 4.2225 (2.1); 4.1988 (6.9); 4.1751 (7.0); 4.1514 (2.3); 3.5005(0.3); 3.3950 (0.6); 3.3352 (356.2); 2.5090 (22.0); 2.5032 (28.0);2.4974 (19.7); 1.2275 (8.2); 1.2038 (16.0); 1.1802 (7.4); 0.8535 (0.4);0.0000 (9.7); −0.0111 (0.5) I-162: ¹H-NMR(300.1 MHz, d₆-DMSO): δ =7.6365 (1.6); 7.6176 (1.8); 7.6062 (2.6); 7.6009 (3.5); 7.5906 (5.4);7.5724 (2.8); 7.5630 (4.3); 7.4204 (0.9); 7.3928 (3.3); 7.3732 (7.0);7.3553 (1.8); 7.3457 (1.8); 7.3280 (2.0); 7.3185 (1.8); 7.2989 (1.2);7.2894 (1.0); 4.9134 (12.5); 4.8877 (0.4); 4.1929 (2.2); 4.1693 (6.8);4.1456 (6.8); 4.1220 (2.2); 3.3288 (67.9); 2.5101 (8.3); 2.5042 (10.5);2.4984 (7.3); 1.2342 (1.5); 1.2086 (7.8); 1.1850 (16.0); 1.1613 (7.4);−0.0001 (2.0) I-163: ¹H-NMR(300.1 MHz, d₆-DMSO): δ = 7.6120 (2.4);7.6063 (2.4); 7.5765 (2.8); 7.5730 (2.8); 7.5522 (1.2); 7.5428 (2.0);7.5230 (2.0); 7.5134 (1.2); 7.4936 (1.1); 7.4446 (1.5); 7.4349 (1.5);7.4209 (3.7); 7.4143 (2.3); 7.4005 (8.4); 7.3788 (1.5); 7.3695 (1.8);7.2229 (0.9); 7.2181 (1.0); 7.2137 (0.9); 7.1912 (1.6); 7.1658 (0.8);7.1613 (0.8); 7.1570 (0.7); 7.1525 (0.6); 4.9291 (12.8); 4.2037 (2.3);4.1800 (6.9); 4.1564 (7.0); 4.1327 (2.2); 3.5477 (0.5); 3.3191 (18.5);2.5137 (8.6); 2.5082 (15.6); 2.5024 (19.4); 2.4965 (13.3); 1.2098 (7.8);1.1861 (16.0); 1.1625 (7.3); −0.0001 (11.6); −0.0112 (0.5) I-164:¹H-NMR(400.0 MHz, CDCl3): δ = 7.7645 (0.6); 7.3332 (0.5); 7.3277 (0.8);7.3131 (0.8); 7.3079 (0.7); 7.2928 (0.9); 7.2872 (0.8); 7.2701 (2.3);7.2663 (1.2); 7.2638 (1.5); 7.2586 (26.8); 7.2515 (3.0); 7.2441 (1.1);7.2400 (1.5); 7.2361 (1.0); 7.2231 (1.0); 7.1329 (1.8); 7.1289 (2.6);7.1233 (0.7); 7.1162 (1.0); 7.1117 (1.9); 7.1088 (1.6); 7.0716 (0.6);7.0692 (0.8); 7.0653 (0.8); 7.0628 (0.9); 7.0557 (0.9); 7.0518 (1.3);7.0495 (1.0); 7.0417 (0.5); 7.0365 (0.7); 7.0330 (1.2); 7.0302 (0.9);7.0269 (0.8); 7.0209 (0.7); 7.0034 (0.7); 6.9994 (0.7); 6.9936 (0.5);5.2688 (1.6); 5.2513 (1.7); 3.7889 (16.0); 3.7719 (1.7); 1.6994 (6.7);1.6868 (1.2); 1.6819 (6.7); 1.6695 (0.8); 1.5352 (2.4); −0.0002 (9.7)I-165: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.7643 (0.9); 7.3183 (0.6); 7.3018(2.1); 7.2981 (0.9); 7.2955 (0.9); 7.2871 (1.1); 7.2833 (2.5); 7.2784(1.0); 7.2742 (1.7); 7.2703 (1.1); 7.2587 (17.6); 7.1355 (1.8); 7.1314(2.4); 7.1258 (0.7); 7.1189 (1.0); 7.1144 (2.0); 7.1113 (1.6); 6.8371(0.6); 6.8219 (2.1); 6.8165 (2.5); 6.8065 (1.3); 6.7991 (3.6); 5.2968(1.1); 5.2595 (1.6); 5.2421 (1.7); 5.2247 (0.5); 3.7853 (16.0); 3.7721(2.7); 1.6969 (6.7); 1.6869 (1.5); 1.6794 (6.6); 1.6695 (1.3); 1.5430(2.1); −0.0002 (6.3) I-166: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4230 (0.7);7.4202 (0.5); 7.4180 (0.6); 7.4094 (0.5); 7.4071 (0.5); 7.4049 (0.6);7.4023 (0.7); 7.3169 (0.9); 7.3131 (0.9); 7.2991 (0.7); 7.2948 (0.6);7.2586 (17.3); 7.2401 (2.3); 7.2361 (1.1); 7.2345 (1.1); 7.2250 (1.2);7.2212 (2.8); 7.2116 (1.6); 7.2091 (1.6); 7.2071 (1.8); 7.2032 (1.1);7.1929 (1.8); 7.1903 (2.6); 7.1743 (0.9); 7.1714 (0.9); 7.1467 (2.2);7.1427 (3.1); 7.1370 (0.7); 7.1298 (1.1); 7.1254 (1.9); 7.1224 (1.5);7.0927 (0.7); 7.0904 (0.7); 7.0690 (1.2); 7.0475 (0.6); 7.0454 (0.6);5.2967 (2.0); 5.2928 (0.6); 5.2753 (1.8); 5.2579 (1.8); 5.2405 (0.5);3.7949 (16.0); 1.7042 (7.4); 1.6868 (7.3); 1.5386 (1.0); −0.0002 (9.6)I-169: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3538 (0.6); 7.3476 (0.6); 7.3323(1.0); 7.3171 (0.6); 7.3109 (0.6); 7.2602 (28.6); 7.2514 (0.8); 7.2481(0.6); 7.1750 (0.6); 7.1536 (0.6); 7.1481 (0.6); 7.1445 (0.5); 7.1348(0.5); 7.1296 (0.6); 7.1233 (0.9); 7.1195 (0.5); 7.1033 (0.7); 7.0983(0.8); 7.0783 (0.6); 7.0355 (0.5); 7.0289 (0.6); 7.0248 (0.5); 6.9246(0.7); 5.1950 (1.6); 5.1777 (1.6); 3.7529 (16.0); 1.6837 (6.5); 1.6663(6.4); 1.5409 (1.9); 0.0079 (0.7); −0.0002 (18.0); −0.0086 (0.9) I-176:¹H-NMR(400.0 MHz, CDCl3): δ = 7.4057 (3.0); 7.4014 (2.7); 7.3945 (1.1);7.3923 (1.0); 7.3878 (1.6); 7.3864 (1.4); 7.3757 (0.6); 7.3010 (1.8);7.2966 (2.0); 7.2903 (0.6); 7.2891 (0.7); 7.2877 (0.6); 7.2851 (0.8);7.2829 (0.8); 7.2766 (1.4); 7.2601 (32.2); 7.1584 (0.9); 7.1428 (0.8);7.1381 (0.5); 6.9279 (0.8); 6.9226 (0.6); 6.9029 (1.3); 6.8970 (0.8);6.8845 (0.8); 6.8822 (0.9); 6.8781 (0.6); 6.8758 (0.5); 6.8323 (0.7);6.8301 (0.7); 6.8274 (0.6); 6.8252 (0.6); 6.8120 (0.6); 6.8099 (0.6);6.8070 (0.6); 5.2991 (5.6); 5.2536 (1.5); 5.2362 (1.5); 3.8008 (16.0);2.7744 (3.0); 1.7044 (6.2); 1.6870 (6.1); 1.5997 (0.9); 0.0080 (0.6);−0.0002 (18.5) I-177: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4213 (1.2); 7.4167(1.6); 7.4078 (7.3); 7.4045 (7.9); 7.3986 (2.9); 7.3937 (2.6); 7.3897(4.8); 7.3806 (1.2); 7.3763 (1.6); 7.3707 (0.5); 7.3666 (0.8); 7.3456(0.7); 7.3004 (1.1); 7.2951 (5.7); 7.2909 (5.8); 7.2862 (2.2); 7.2842(1.9); 7.2812 (1.8); 7.2782 (2.6); 7.2761 (3.1); 7.2709 (3.8); 7.2600(22.9); 7.1810 (1.3); 7.1655 (1.2); 7.1605 (2.6); 7.1449 (2.4); 7.1401(1.4); 7.1247 (1.3); 6.9274 (1.3); 6.9219 (2.7); 6.9167 (2.0); 6.9061(1.5); 6.9037 (2.3); 6.8973 (3.0); 6.8922 (2.2); 6.8855 (2.2); 6.8832(2.6); 6.8792 (1.3); 6.8769 (1.3); 6.8622 (3.2); 6.8592 (2.6); 6.8570(2.3); 6.8416 (1.9); 6.8395 (1.8); 6.8367 (1.6); 6.8346 (1.3); 6.0115(1.1); 5.3340 (1.2); 5.3165 (4.5); 5.3024 (0.9); 5.2990 (4.5); 5.2815(1.2); 1.7566 (16.0); 1.7391 (15.8); 1.7038 (1.2); 1.6864 (1.2); 0.0080(0.8); −0.0002 (29.9); −0.0085 (0.9) I-178: ¹H-NMR(400.0 MHz, CDCl3): δ= 7.4466 (0.6); 7.4404 (0.6); 7.4251 (1.1); 7.4099 (0.6); 7.4036 (0.6);7.2615 (16.5); 7.1948 (0.7); 7.1755 (0.6); 7.1708 (1.1); 7.1660 (0.6);7.1527 (0.8); 7.1508 (0.6); 7.1477 (0.7); 7.1405 (0.6); 7.1327 (0.6);7.1298 (0.6); 7.1269 (0.6); 7.1233 (0.9); 7.1214 (1.1); 7.0013 (0.6);6.9976 (0.6); 6.9826 (0.6); 5.1792 (1.6); 5.1618 (1.6); 3.7555 (16.0);1.6871 (6.6); 1.6697 (6.5); 1.5496 (1.0); −0.0002 (10.7) I-179:¹H-NMR(400.0 MHz, CDCl3): δ = 7.4467 (0.6); 7.4406 (0.7); 7.4253 (1.2);7.4100 (0.7); 7.4038 (0.7); 7.2617 (13.1); 7.2161 (0.5); 7.1948 (1.0);7.1752 (0.9); 7.1708 (1.5); 7.1663 (0.9); 7.1526 (1.1); 7.1478 (1.0);7.1406 (0.9); 7.1325 (0.8); 7.1270 (0.9); 7.1215 (1.5); 7.1139 (0.7);7.1083 (0.5); 6.9976 (1.0); 6.9820 (1.0); 5.1967 (0.5); 5.1793 (1.7);5.1619 (1.7); 5.1445 (0.5); 3.7555 (16.0); 1.6871 (7.0); 1.6697 (7.0);−0.0002 (8.0) II-01: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4677 (1.3);7.4591 (5.0); 7.4564 (4.7); 7.4541 (3.9); 7.4485 (8.2); 7.4424 (10.4);7.4331 (1.3); 7.3315 (1.2); 7.3148 (1.5); 7.3108 (2.8); 7.2965 (4.9);7.2944 (5.1); 7.2905 (4.1); 7.2876 (5.2); 7.2785 (4.2); 7.2728 (4.3);7.0697 (1.1); 7.0654 (1.1); 7.0482 (1.8); 7.0442 (1.9); 7.0272 (0.9);7.0230 (1.0); 6.9311 (1.3); 6.9257 (2.1); 6.9200 (1.5); 6.9052 (1.3);6.9000 (2.2); 6.8940 (1.6); 6.8856 (2.4); 6.8835 (2.7); 6.8808 (2.0);6.8785 (1.7); 6.8653 (2.1); 6.8633 (2.2); 6.8605 (2.0); 4.2659 (16.0);3.2925 (0.7); 2.6742 (1.3); 2.6695 (1.8); 2.6650 (1.3); 2.5996 (0.6);2.5955 (0.5); 2.5587 (0.9); 2.5541 (1.8); 2.5495 (2.6); 2.5448 (2.4);2.5401 (2.1); 2.5230 (8.0); 2.5183 (11.4); 2.5095 (107.9); 2.5051(223.3); 2.5005 (302.9); 2.4959 (216.2); 2.4914 (102.7); 2.4636 (1.0);2.4585 (0.5); 2.3318 (1.4); 2.3273 (1.9); 2.3227 (1.4); 0.0080 (1.2);−0.0002 (38.8); −0.0085 (1.5) II-02: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =7.4592 (6.1); 7.4490 (9.5); 7.4426 (11.3); 7.3322 (1.4); 7.3117 (3.2);7.2961 (6.6); 7.2910 (5.1); 7.2874 (6.1); 7.2785 (4.9); 7.2727 (4.4);7.0728 (1.2); 7.0663 (1.4); 7.0511 (2.1); 7.0467 (2.3); 7.0320 (1.1);7.0255 (1.2); 6.9360 (1.6); 6.9306 (2.5); 6.9249 (1.8); 6.9102 (1.6);6.9049 (2.6); 6.8991 (1.9); 6.8843 (3.1); 6.8641 (2.5); 6.8613 (2.4);4.2979 (16.0); 3.5676 (1.2); 3.2987 (5.8); 2.6747 (3.1); 2.6701 (4.3);2.6655 (3.1); 2.6136 (0.8); 2.5879 (0.8); 2.5492 (2.1); 2.5447 (3.9);2.5234 (27.4); 2.5188 (38.3); 2.5100 (276.3); 2.5055 (561.0); 2.5010(754.3); 2.4964 (546.2); 2.4919 (268.5); 2.4351 (1.1); 2.4003 (0.8);2.3956 (0.7); 2.3905 (0.5); 2.3323 (3.6); 2.3277 (4.8); 2.3232 (3.7);0.0080 (2.2); −0.0002 (62.8); −0.0085 (3.1) II-04: ¹H-NMR(400.0 MHz,d₆-DMSO): δ = 7.4612 (9.0); 7.4559 (6.4); 7.4531 (10.2); 7.4452 (10.4);7.4411 (3.6); 7.4352 (1.3); 7.4201 (0.6); 7.4097 (0.8); 7.4034 (0.9);7.3498 (1.5); 7.3333 (1.9); 7.3292 (3.3); 7.3128 (3.9); 7.3082 (3.5);7.3047 (5.6); 7.3010 (3.6); 7.2973 (5.1); 7.2943 (4.6); 7.2914 (5.1);7.2882 (4.6); 7.2845 (3.1); 7.2807 (4.2); 7.1042 (1.4); 7.0997 (1.4);7.0828 (2.4); 7.0784 (2.4); 7.0636 (1.1); 7.0616 (1.2); 7.0571 (1.2);6.9641 (1.8); 6.9587 (2.8); 6.9529 (1.9); 6.9384 (1.8); 6.9332 (2.9);6.9272 (2.0); 6.9054 (2.9); 6.9033 (3.2); 6.9006 (2.6); 6.8984 (2.4);6.8852 (2.6); 6.8831 (2.7); 6.8802 (2.6); 6.8782 (2.2); 6.5483 (0.7);6.5083 (0.6); 4.6410 (16.0); 3.7305 (1.2); 3.5917 (10.8); 3.5799 (12.4);3.5679 (11.6); 3.3549 (2.2); 2.8119 (10.1); 2.7998 (11.2); 2.7880 (9.8);2.6740 (1.0); 2.6694 (1.5); 2.6647 (1.1); 2.5228 (4.6); 2.5182 (6.6);2.5094 (79.9); 2.5049 (168.4); 2.5003 (230.8); 2.4958 (164.0); 2.4912(76.9); 2.4589 (0.5); 2.4546 (0.8); 2.4497 (1.2); 2.4453 (1.1); 2.3806(0.5); 2.3316 (1.1); 2.3271 (1.4); 2.3226 (1.1); 0.0080 (1.5); −0.0002(47.9); −0.0085 (1.8) II-05: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4597(5.9); 7.4516 (6.9); 7.4437 (7.2); 7.4341 (1.0); 7.3407 (1.0); 7.3241(1.3); 7.3201 (2.2); 7.3117 (0.8); 7.3013 (4.7); 7.2939 (3.6); 7.2911(3.1); 7.2877 (2.9); 7.2843 (3.8); 7.2774 (3.0); 7.0944 (1.0); 7.0897(1.0); 7.0730 (1.7); 7.0683 (1.7); 7.0536 (0.8); 7.0517 (0.8); 7.0471(0.8); 6.9550 (1.2); 6.9496 (2.0); 6.9439 (1.3); 6.9293 (1.2); 6.9241(2.0); 6.9183 (1.4); 6.9003 (2.2); 6.8975 (1.8); 6.8819 (1.8); 6.8801(1.9); 6.8772 (1.8); 5.9152 (0.6); 5.8889 (0.8); 5.8720 (0.9); 5.8458(0.8); 5.7527 (16.0); 5.3459 (1.4); 5.3422 (1.5); 5.3026 (1.2); 5.2990(1.2); 5.2357 (1.5); 5.2324 (1.5); 5.2095 (1.4); 5.2063 (1.4); 4.5838(9.4); 3.4125 (2.8); 3.4092 (2.0); 3.3976 (2.9); 2.5101 (12.4); 2.5057(28.0); 2.5011 (39.9); 2.4966 (30.1); 2.4922 (15.6); −0.0002 (7.0)II-06: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4659 (1.8); 7.4600 (8.1);7.4515 (9.7); 7.4477 (6.6); 7.4439 (11.4); 7.4409 (5.1); 7.4343 (2.1);7.4096 (0.8); 7.4050 (0.8); 7.3970 (0.9); 7.3921 (0.9); 7.3381 (1.5);7.3216 (1.8); 7.3175 (3.3); 7.3091 (1.1); 7.2992 (6.8); 7.2912 (5.2);7.2893 (4.9); 7.2859 (4.2); 7.2817 (5.7); 7.2751 (5.0); 7.2689 (1.4);7.0922 (1.2); 7.0903 (1.4); 7.0839 (1.4); 7.0689 (2.4); 7.0627 (2.5);7.0496 (1.2); 7.0477 (1.3); 7.0432 (1.3); 7.0413 (1.3); 6.9524 (1.8);6.9469 (2.8); 6.9412 (2.0); 6.9266 (1.8); 6.9213 (3.0); 6.9155 (2.1);6.8948 (2.8); 6.8928 (3.2); 6.8900 (2.7); 6.8880 (2.6); 6.8746 (2.6);6.8726 (2.8); 6.8697 (2.7); 6.8677 (2.4); 5.7531 (16.0); 4.5178 (12.9);2.7229 (3.9); 2.7043 (4.8); 2.6853 (4.3); 2.6749 (0.6); 2.6702 (0.6);2.5236 (1.0); 2.5189 (1.5); 2.5102 (22.4); 2.5057 (48.9); 2.5011 (69.0);2.4965 (50.9); 2.4920 (26.2); 1.5622 (2.0); 1.5434 (3.6); 1.5246 (3.8);1.5060 (2.3); 1.4874 (0.7); 0.8847 (7.7); 0.8661 (16.0); 0.8474 (7.2);−0.0002 (12.8); −0.0085 (0.6) II-07: ¹H-NMR(400.0 MHz, d₆-DMSO): δ =7.6913 (1.0); 7.6823 (1.3); 7.6792 (1.0); 7.6728 (1.3); 7.6672 (1.2);7.6036 (1.4); 7.5635 (1.6); 7.4630 (3.1); 7.4581 (2.1); 7.4551 (3.3);7.4524 (2.0); 7.4469 (3.2); 7.4419 (1.1); 7.4296 (0.7); 7.4233 (2.1);7.4137 (2.7); 7.4068 (2.9); 7.3572 (0.6); 7.3407 (0.7); 7.3366 (1.2);7.3202 (1.3); 7.3159 (1.0); 7.3088 (1.9); 7.3018 (1.9); 7.2983 (1.6);7.2947 (1.4); 7.2928 (1.6); 7.2885 (1.0); 7.2848 (1.4); 7.0949 (0.8);7.0904 (0.8); 6.9767 (0.6); 6.9713 (0.9); 6.9654 (0.6); 6.9511 (0.6);6.9458 (1.0); 6.9399 (0.6); 6.9103 (0.9); 6.9083 (1.0); 6.9055 (0.9);6.9034 (0.8); 6.8902 (0.8); 6.8881 (0.9); 6.8852 (0.8); 6.8831 (0.7);6.5494 (2.3); 6.5093 (2.1); 4.7574 (4.4); 3.5677 (3.8); 3.3165 (0.8);3.2439 (0.6); 2.5232 (1.4); 2.5185 (2.0); 2.5098 (25.7); 2.5053 (54.0);2.5007 (74.1); 2.4961 (53.5); 2.4916 (25.8); 2.4766 (2.5); 2.4565 (1.8);1.4641 (1.6); 1.4454 (2.7); 1.4266 (2.8); 1.4080 (1.7); 1.2353 (0.9);0.8610 (7.7); 0.8427 (16.0); 0.8242 (6.9); −0.0002 (8.7) II-08:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.6397 (1.8); 7.6343 (1.6); 7.6203(2.3); 7.6159 (2.0); 7.4867 (2.0); 7.4678 (1.0); 7.4610 (4.1); 7.4519(5.4); 7.4448 (7.4); 7.4351 (1.0); 7.4203 (0.6); 7.4112 (0.7); 7.4066(0.6); 7.3979 (2.4); 7.3879 (1.8); 7.3823 (3.8); 7.3797 (3.7); 7.3697(0.9); 7.3657 (0.7); 7.3378 (0.9); 7.3214 (1.2); 7.3171 (1.9); 7.3082(0.6); 7.3008 (2.9); 7.2985 (3.6); 7.2927 (2.0); 7.2895 (3.0); 7.2856(2.1); 7.2807 (3.4); 7.2744 (2.6); 7.0896 (0.7); 7.0876 (0.8); 7.0832(0.8); 7.0812 (0.8); 7.0682 (1.2); 7.0662 (1.3); 7.0618 (1.3); 7.0599(1.3); 7.0471 (0.6); 7.0450 (0.7); 7.0406 (0.6); 7.0386 (0.6); 6.9515(1.0); 6.9460 (1.5); 6.9403 (1.0); 6.9257 (1.0); 6.9204 (1.6); 6.9145(1.1); 6.8868 (1.5); 6.8847 (1.7); 6.8818 (1.4); 6.8798 (1.3); 6.8665(1.4); 6.8644 (1.4); 6.8615 (1.4); 6.8594 (1.2); 6.5233 (3.3); 6.4833(3.1); 4.4480 (8.9); 2.8181 (1.9); 2.8000 (5.9); 2.7819 (6.0); 2.7638(2.0); 2.6701 (0.5); 2.5235 (1.3); 2.5189 (2.0); 2.5101 (30.5); 2.5056(65.0); 2.5010 (89.4); 2.4964 (63.7); 2.4919 (30.1); 2.4388 (32.4);2.3279 (0.6); 1.2344 (1.0); 1.1270 (7.5); 1.1089 (16.0); 1.0908 (7.2);−0.0002 (11.7) II-09: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4605 (1.5);7.4514 (1.8); 7.4443 (2.2); 7.3167 (0.7); 7.3005 (1.0); 7.2975 (1.3);7.2886 (1.1); 7.2848 (0.7); 7.2800 (1.2); 7.2736 (0.8); 6.9426 (0.5);6.9170 (0.5); 6.8864 (0.6); 6.8843 (0.6); 6.8815 (0.5); 6.8662 (0.5);4.4522 (1.4); 3.3124 (3.9); 2.5228 (1.5); 2.5181 (2.1); 2.5093 (26.2);2.5048 (54.8); 2.5002 (74.9); 2.4957 (53.0); 2.4911 (24.7); 1.2204(16.0); −0.0002 (11.8) II-10: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4582(1.7); 7.4495 (2.0); 7.4421 (2.4); 7.4003 (0.6); 7.3293 (0.6); 7.3110(1.7); 7.2918 (2.4); 7.2820 (0.9); 7.2751 (1.1); 7.2711 (1.0); 7.2387(1.7); 7.2264 (1.0); 7.2196 (1.0); 7.0634 (0.5); 7.0589 (0.5); 6.9355(0.6); 6.9103 (0.6); 6.8877 (0.7); 6.8672 (0.6); 4.4795 (1.5); 3.3118(16.0); 2.9714 (0.6); 2.9534 (1.2); 2.9470 (0.7); 2.9322 (1.1); 2.8076(1.0); 2.7866 (1.1); 2.7687 (0.6); 2.6740 (0.8); 2.6694 (1.1); 2.6648(0.9); 2.5229 (3.4); 2.5181 (4.9); 2.5094 (65.6); 2.5049 (138.2); 2.5003(189.2); 2.4958 (135.0); 2.4913 (63.8); 2.4507 (1.1); 2.4457 (0.7);2.3317 (0.8); 2.3271 (1.1); 2.3225 (0.8); 0.0079 (0.6); −0.0002 (20.9);−0.0085 (0.8) II-11: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4678 (1.1);7.4612 (4.0); 7.4522 (5.1); 7.4450 (6.2); 7.4353 (1.1); 7.3381 (0.8);7.3217 (0.9); 7.3175 (1.7); 7.3076 (0.6); 7.3010 (2.6); 7.2977 (3.6);7.2920 (1.9); 7.2892 (2.9); 7.2850 (2.2); 7.2805 (3.5); 7.2739 (2.6);7.0904 (0.6); 7.0884 (0.7); 7.0838 (0.7); 7.0820 (0.8); 7.0688 (1.1);7.0670 (1.2); 7.0624 (1.3); 7.0608 (1.3); 7.0478 (0.6); 7.0458 (0.7);7.0413 (0.7); 7.0394 (0.6); 6.9539 (0.9); 6.9484 (1.5); 6.9427 (1.0);6.9281 (1.0); 6.9227 (1.5); 6.9169 (1.1); 6.8870 (1.4); 6.8849 (1.6);6.8821 (1.4); 6.8800 (1.4); 6.8667 (1.3); 6.8647 (1.4); 6.8618 (1.4);6.8597 (1.3); 5.7530 (16.0); 4.4682 (8.4); 2.9324 (2.6); 2.9191 (3.8);2.9050 (3.1); 2.5188 (0.7); 2.5101 (11.8); 2.5055 (26.3); 2.5009 (37.8);2.4964 (28.5); 2.4918 (15.1); 1.6250 (0.6); 1.5973 (3.0); 1.5847 (2.5);1.5700 (1.3); 1.5030 (1.4); 1.4914 (1.5); −0.0002 (8.6) II-12:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4608 (6.4); 7.4524 (7.3); 7.4485(4.8); 7.4447 (8.3); 7.3453 (1.1); 7.3289 (1.3); 7.3246 (2.4); 7.3082(2.8); 7.3024 (4.6); 7.2986 (2.7); 7.2945 (3.7); 7.2923 (3.4); 7.2885(3.7); 7.2855 (3.7); 7.2783 (3.3); 7.0970 (1.0); 7.0907 (1.0); 7.0758(1.8); 7.0698 (1.8); 7.0544 (0.9); 7.0501 (0.8); 6.9567 (1.3); 6.9512(2.1); 6.9455 (1.4); 6.9309 (1.3); 6.9258 (2.1); 6.9198 (1.4); 6.8999(2.1); 6.8979 (2.3); 6.8950 (1.9); 6.8796 (1.9); 6.8776 (2.0); 6.8748(1.9); 6.8726 (1.7); 4.5654 (4.1); 3.5675 (4.6); 3.3120 (16.0); 3.1682(0.6); 2.7559 (1.9); 2.7373 (2.2); 2.7180 (2.0); 2.6740 (1.4); 2.6694(2.0); 2.6647 (1.4); 2.5988 (0.8); 2.5228 (5.9); 2.5181 (8.6); 2.5094(116.8); 2.5049 (246.0); 2.5003 (336.5); 2.4957 (238.9); 2.4912 (112.9);2.4397 (0.6); 2.4123 (0.5); 2.3317 (1.4); 2.3270 (2.0); 2.3225 (1.5);1.5031 (1.1); 1.4842 (0.8); 1.2483 (9.4); 0.8748 (1.9); 0.8580 (6.5);0.8404 (2.3); 0.0080 (1.9); −0.0002 (58.5); −0.0085 (2.3) II-13:¹H-NMR(400.0 MHz, d₆-DMSO): δ = 7.4584 (8.7); 7.4500 (10.1); 7.4461(6.9); 7.4423 (11.6); 7.4389 (4.9); 7.4341 (4.5); 7.4302 (5.0); 7.4133(7.0); 7.3981 (1.0); 7.3930 (0.9); 7.3769 (2.5); 7.3729 (3.4); 7.3682(1.5); 7.3558 (8.0); 7.3517 (3.4); 7.3407 (2.5); 7.3373 (4.7); 7.3260(2.4); 7.3221 (4.0); 7.3184 (4.0); 7.3141 (4.1); 7.3047 (4.2); 7.2969(8.7); 7.2933 (6.1); 7.2891 (6.0); 7.2868 (5.7); 7.2834 (4.8); 7.2798(5.4); 7.2769 (5.3); 7.2728 (4.9); 7.0902 (1.3); 7.0882 (1.5); 7.0838(1.5); 7.0819 (1.5); 7.0687 (2.3); 7.0668 (2.5); 7.0624 (2.5); 7.0476(1.2); 7.0455 (1.3); 7.0411 (1.3); 7.0392 (1.2); 6.9493 (1.8); 6.9438(2.9); 6.9381 (2.0); 6.9235 (1.9); 6.9183 (3.1); 6.9124 (2.1); 6.8967(3.0); 6.8947 (3.4); 6.8918 (2.7); 6.8897 (2.5); 6.8764 (2.7); 6.8744(2.9); 6.8716 (2.7); 6.8695 (2.4); 5.7530 (16.0); 4.5278 (14.7); 3.9323(14.6); 2.5231 (0.9); 2.5184 (1.4); 2.5096 (30.8); 2.5051 (67.2); 2.5005(93.6); 2.4960 (68.4); 2.4914 (33.5); 2.4359 (0.5); 2.3319 (0.6); 2.3274(0.7); 2.3227 (0.6); −0.0002 (12.0); −0.0085 (0.5) II-14: ¹H-NMR(400.0MHz, CDCl3): δ = 7.4021 (0.6); 7.3954 (3.7); 7.3906 (3.8); 7.3829 (2.3);7.3779 (2.3); 7.3706 (0.6); 7.3669 (0.8); 7.2821 (2.2); 7.2775 (2.5);7.2692 (1.7); 7.2618 (22.2); 7.2581 (2.4); 7.1197 (0.5); 7.1039 (0.6);7.0991 (1.2); 7.0833 (1.2); 7.0786 (0.8); 7.0628 (0.7); 6.9710 (0.6);6.9654 (1.0); 6.9598 (0.7); 6.9454 (0.6); 6.9399 (1.0); 6.9342 (0.7);6.8362 (0.6); 6.8298 (0.6); 6.8209 (1.3); 6.8170 (1.9); 6.8110 (1.1);6.8091 (0.8); 6.7998 (1.0); 6.7966 (1.3); 6.7904 (0.5); 5.2979 (11.6);4.8230 (7.5); 3.0865 (2.1); 3.0682 (7.0); 3.0499 (7.2); 3.0316 (2.2);1.2574 (7.5); 1.2392 (16.0); 1.2208 (7.2); −0.0002 (8.9) III-001:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3870 (1.0); 7.3827 (1.2); 7.3678 (2.0);7.3637 (2.3); 7.3531 (1.1); 7.3493 (2.3); 7.3393 (5.0); 7.3364 (5.7);7.3310 (2.8); 7.3211 (5.4); 7.3074 (2.5); 7.3004 (1.8); 7.2887 (1.7);7.2830 (5.2); 7.2787 (4.7); 7.2741 (2.2); 7.2686 (1.5); 7.2592 (20.6);7.1839 (1.4); 7.1649 (2.1); 7.1462 (0.9); 7.0343 (1.3); 7.0312 (1.2);7.0135 (1.3); 7.0098 (2.1); 7.0061 (1.3); 6.9885 (1.1); 6.9854 (1.0);6.7256 (0.7); 5.2952 (11.6); 4.8957 (3.1); 4.8718 (16.0); 4.8652 (3.6);4.8618 (2.6); 3.9428 (3.6); 3.9276 (3.5); 1.7660 (11.9); 1.5854 (0.8);1.2557 (0.8); −0.0002 (6.8) III-002: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3748 (0.7); 7.3705 (0.9); 7.3555 (1.5); 7.3517 (2.1); 7.3375 (4.2);7.3356 (4.7); 7.3327 (3.0); 7.3301 (2.3); 7.3236 (1.9); 7.3197 (3.8);7.3176 (3.4); 7.3089 (1.2); 7.3057 (1.7); 7.3005 (1.2); 7.2967 (1.1);7.2881 (0.8); 7.2838 (1.1); 7.2774 (3.6); 7.2732 (3.6); 7.2688 (1.7);7.2604 (15.8); 7.2530 (1.7); 7.1828 (0.9); 7.1812 (1.0); 7.1620 (1.4);7.1442 (0.6); 7.1427 (0.6); 7.0377 (0.9); 7.0345 (0.9); 7.0169 (0.9);7.0130 (1.5); 7.0094 (1.0); 6.9918 (0.8); 6.9886 (0.8); 6.6878 (0.6);5.2956 (16.0); 4.8041 (11.3); 2.8234 (0.7); 2.8141 (1.0); 2.8055 (1.0);2.7962 (0.8); 2.0419 (0.6); 1.6016 (0.5); 1.2572 (0.9); 0.8631 (0.8);0.8491 (1.8); 0.8454 (2.8); 0.8426 (1.3); 0.8317 (2.6); 0.8276 (2.1);0.8247 (1.2); 0.8143 (0.9); 0.6284 (0.9); 0.6184 (1.8); 0.6153 (2.0);0.6113 (2.0); 0.6099 (2.0); 0.6057 (2.0); 0.6020 (1.8); 0.5883 (0.7);−0.0002 (5.3) III-003: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3866 (1.2);7.3823 (1.4); 7.3742 (0.6); 7.3672 (2.2); 7.3630 (2.5); 7.3541 (1.4);7.3504 (1.8); 7.3486 (1.9); 7.3423 (4.0); 7.3400 (5.4); 7.3372 (6.3);7.3317 (3.3); 7.3296 (1.8); 7.3259 (2.7); 7.3219 (5.7); 7.3196 (5.1);7.3141 (1.4); 7.3121 (1.5); 7.3103 (1.8); 7.3082 (2.8); 7.3064 (2.0);7.3021 (1.8); 7.2989 (1.5); 7.2898 (2.0); 7.2836 (5.7); 7.2793 (5.3);7.2747 (2.4); 7.2694 (1.6); 7.2663 (2.4); 7.2592 (37.8); 7.1877 (1.2);7.1860 (1.4); 7.1844 (1.4); 7.1650 (2.0); 7.1491 (0.8); 7.1474 (0.9);7.1458 (0.9); 7.1444 (0.8); 7.0377 (1.4); 7.0345 (1.3); 7.0169 (1.4);7.0131 (2.2); 7.0094 (1.4); 6.9919 (1.2); 6.9887 (1.1); 6.7103 (0.6);5.9472 (0.6); 5.9336 (1.3); 5.9213 (0.8); 5.9078 (1.4); 5.9043 (0.8);5.8941 (0.8); 5.8906 (1.5); 5.8783 (0.9); 5.8772 (0.9); 5.8649 (1.5);5.8512 (0.7); 5.2963 (9.6); 5.2791 (0.9); 5.2749 (2.1); 5.2717 (2.2);5.2674 (1.1); 5.2362 (0.8); 5.2320 (1.8); 5.2287 (1.9); 5.2245 (1.0);5.1885 (1.1); 5.1849 (2.5); 5.1816 (2.4); 5.1780 (1.0); 5.1628 (1.0);5.1592 (2.3); 5.1558 (2.2); 5.1522 (0.9); 4.8601 (16.0); 4.0348 (1.4);4.0309 (2.4); 4.0269 (1.6); 4.0202 (2.5); 4.0167 (4.0); 4.0131 (2.4);4.0065 (1.4); 4.0025 (2.2); 3.9986 (1.2); 1.5654 (5.0); 0.0079 (0.6);−0.0002 (18.2); −0.0085 (0.7) III-004: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3122 (0.9); 7.3081 (1.2); 7.3068 (1.4); 7.3024 (0.9); 7.2981 (0.7);7.2956 (0.8); 7.2920 (3.2); 7.2905 (4.9); 7.2866 (5.4); 7.2843 (3.0);7.2810 (1.9); 7.2758 (2.8); 7.2719 (7.8); 7.2700 (5.6); 7.2667 (3.3);7.2641 (6.6); 7.2625 (5.7); 7.2596 (38.6); 7.2510 (4.7); 7.2464 (2.1);7.2449 (2.1); 7.2270 (0.6); 7.1570 (4.2); 7.1529 (5.2); 7.1472 (1.4);7.1406 (2.2); 7.1379 (1.7); 7.1360 (4.2); 7.1326 (3.4); 7.0974 (0.5);7.0902 (4.5); 7.0847 (1.3); 7.0761 (0.7); 7.0733 (1.4); 7.0688 (6.3);7.0635 (1.4); 7.0608 (0.6); 7.0521 (1.2); 7.0466 (3.5); 6.6980 (0.6);5.9491 (0.6); 5.9354 (1.3); 5.9232 (0.8); 5.9219 (0.8); 5.9096 (1.5);5.9062 (0.8); 5.8960 (0.8); 5.8925 (1.6); 5.8803 (0.9); 5.8789 (0.9);5.8667 (1.6); 5.8531 (0.8); 5.2970 (7.6); 5.2791 (0.9); 5.2748 (2.1);5.2716 (2.2); 5.2673 (1.0); 5.2361 (0.8); 5.2318 (1.9); 5.2286 (1.9);5.2243 (0.9); 5.1882 (1.0); 5.1846 (2.5); 5.1812 (2.4); 5.1776 (0.9);5.1625 (0.9); 5.1589 (2.3); 5.1555 (2.2); 5.1519 (0.9); 4.8824 (16.0);4.0374 (1.2); 4.0334 (2.1); 4.0295 (1.4); 4.0228 (2.2); 4.0192 (3.7);4.0155 (2.2); 4.0089 (1.3); 4.0049 (2.1); 4.0009 (1.2); −0.0002 (16.4)III-005: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3116 (0.6); 7.3075 (0.8);7.3062 (1.0); 7.3018 (0.6); 7.2977 (0.6); 7.2950 (0.6); 7.2909 (4.3);7.2899 (4.4); 7.2859 (2.1); 7.2837 (1.8); 7.2778 (3.0); 7.2750 (2.3);7.2713 (4.7); 7.2690 (4.8); 7.2654 (1.8); 7.2635 (1.6); 7.2603 (20.1);7.2570 (3.0); 7.2555 (3.4); 7.2508 (0.8); 7.2483 (0.5); 7.2449 (1.3);7.2436 (1.3); 7.1614 (2.9); 7.1574 (3.6); 7.1516 (1.0); 7.1449 (1.5);7.1422 (1.1); 7.1403 (2.9); 7.1370 (2.2); 7.0926 (3.1); 7.0871 (0.9);7.0783 (0.5); 7.0757 (1.0); 7.0711 (4.3); 7.0658 (0.9); 7.0544 (0.9);7.0490 (2.4); 5.2965 (16.0); 4.8572 (10.2); 3.2647 (2.2); 3.2505 (2.5);3.2471 (2.5); 3.2328 (2.2); 1.0479 (0.5); 1.0280 (0.9); 1.0080 (0.6);0.5572 (0.8); 0.5454 (1.9); 0.5423 (2.4); 0.5400 (1.3); 0.5372 (1.0);0.5309 (1.1); 0.5252 (2.3); 0.5222 (1.9); 0.5109 (0.9); 0.2743 (0.9);0.2628 (2.6); 0.2604 (2.2); 0.2508 (1.9); 0.2480 (2.6); 0.2363 (0.6);−0.0002 (8.0) III-006: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3125 (0.6);7.3084 (0.8); 7.3069 (0.9); 7.3025 (0.6); 7.2958 (0.7); 7.2907 (3.2);7.2885 (3.0); 7.2842 (1.8); 7.2754 (3.4); 7.2722 (4.7); 7.2704 (3.6);7.2661 (3.8); 7.2636 (3.3); 7.2596 (29.3); 7.2530 (3.3); 7.2476 (1.3);7.2459 (1.4); 7.1591 (2.8); 7.1549 (3.2); 7.1492 (0.9); 7.1427 (1.4);7.1399 (1.1); 7.1381 (2.7); 7.1347 (2.2); 7.0918 (2.9); 7.0863 (0.9);7.0749 (0.9); 7.0704 (4.0); 7.0651 (1.0); 7.0537 (0.8); 7.0483 (2.3);5.2972 (16.0); 4.8798 (10.2); 4.1930 (2.8); 4.1866 (2.9); 4.1793 (2.8);4.1729 (2.8); 2.2746 (2.3); 2.2682 (4.9); 2.2618 (2.2); −0.0002 (11.6)III-007: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3056 (0.5); 7.3041 (0.6);7.2895 (1.4); 7.2879 (2.2); 7.2848 (2.2); 7.2816 (1.2); 7.2794 (0.9);7.2717 (2.2); 7.2694 (3.2); 7.2676 (2.5); 7.2625 (3.1); 7.2599 (19.0);7.2559 (1.7); 7.2495 (2.3); 7.2440 (0.9); 7.2424 (1.0); 7.1546 (1.9);7.1505 (2.3); 7.1449 (0.6); 7.1382 (1.0); 7.1355 (0.7); 7.1336 (1.9);7.1302 (1.5); 7.0905 (2.0); 7.0849 (0.6); 7.0735 (0.6); 7.0690 (2.8);7.0637 (0.6); 7.0523 (0.6); 7.0469 (1.6); 5.2970 (3.7); 4.8574 (7.0);3.2283 (1.7); 3.2118 (2.5); 3.1960 (1.7); 1.8661 (0.7); 1.8493 (0.9);1.8325 (0.8); 1.5713 (2.6); 0.9560 (16.0); 0.9513 (1.2); 0.9392 (15.4);0.9343 (0.8); −0.0002 (7.5) III-008: ¹H-NMR(400.0 MHz, CDCl3): δ =7.5185 (0.7); 7.3843 (0.9); 7.3692 (1.1); 7.3636 (1.6); 7.3490 (1.9);7.3444 (1.3); 7.3293 (1.4); 7.2596 (116.5); 7.1371 (3.4); 7.1314 (1.9);7.1252 (4.3); 7.1198 (2.5); 7.1142 (5.1); 7.1114 (2.3); 7.1084 (3.2);7.1023 (6.2); 7.0939 (0.7); 7.0901 (1.0); 7.0877 (1.0); 7.0837 (1.0);7.0812 (0.9); 7.0364 (1.9); 7.0326 (2.7); 7.0301 (2.2); 7.0139 (4.1);7.0111 (3.2); 7.0077 (2.2); 6.9994 (4.9); 6.9955 (1.5); 6.9935 (1.8);6.9905 (2.0); 6.9872 (2.1); 6.9792 (6.0); 6.9766 (4.1); 6.9734 (1.7);6.9620 (1.3); 6.9563 (3.4); 6.6799 (0.7); 5.9590 (0.6); 5.9454 (1.4);5.9330 (1.0); 5.9196 (1.5); 5.9161 (0.8); 5.9060 (0.8); 5.9024 (1.6);5.8891 (1.0); 5.8767 (1.6); 5.8630 (0.8); 5.2906 (1.0); 5.2863 (2.2);5.2831 (2.2); 5.2788 (1.0); 5.2476 (0.9); 5.2433 (2.0); 5.2402 (2.0);5.2358 (0.9); 5.1969 (1.1); 5.1933 (2.5); 5.1899 (2.3); 5.1864 (1.0);5.1711 (1.0); 5.1675 (2.3); 5.1642 (2.2); 5.1605 (0.9); 4.8613 (16.0);4.0433 (1.3); 4.0393 (2.2); 4.0352 (1.4); 4.0251 (4.0); 4.0150 (1.5);4.0109 (2.2); 1.5454 (4.1); 0.0080 (1.5); −0.0002 (43.8); −0.0085 (1.6)III-009: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5187 (0.5); 7.3846 (0.8);7.3698 (1.2); 7.3640 (1.6); 7.3496 (1.8); 7.3447 (1.3); 7.3297 (1.3);7.2599 (86.0); 7.1351 (3.4); 7.1299 (1.9); 7.1234 (4.3); 7.1179 (2.4);7.1122 (5.8); 7.1091 (2.3); 7.1060 (2.8); 7.1005 (4.9); 7.0907 (0.9);7.0881 (0.8); 7.0841 (0.8); 7.0817 (0.8); 7.0356 (1.7); 7.0318 (2.6);7.0293 (2.1); 7.0131 (4.3); 7.0103 (3.1); 6.9975 (4.8); 6.9914 (2.7);6.9856 (2.0); 6.9804 (2.5); 6.9773 (5.3); 6.9716 (1.6); 6.9602 (1.1);6.9546 (3.2); 6.5958 (0.7); 5.2982 (0.6); 4.8225 (15.7); 3.4107 (1.8);3.3931 (3.7); 3.3781 (3.6); 3.3605 (1.8); 1.6093 (0.8); 1.5909 (2.0);1.5849 (0.9); 1.5727 (3.1); 1.5669 (1.8); 1.5505 (5.6); 1.5363 (1.3);1.4439 (0.7); 1.4257 (2.0); 1.4066 (2.6); 1.3872 (2.6); 1.3692 (1.6);1.3509 (0.6); 0.9602 (7.7); 0.9419 (16.0); 0.9236 (6.5); 0.0080 (1.0);−0.0002 (31.8); −0.0085 (1.0) III-010: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3737 (1.0); 7.3586 (1.5); 7.3533 (1.9); 7.3383 (2.7); 7.3337 (2.2);7.3271 (4.7); 7.3239 (7.9); 7.3224 (6.9); 7.3176 (7.5); 7.3134 (5.0);7.3114 (7.1); 7.3094 (6.9); 7.3030 (2.0); 7.2969 (1.9); 7.2930 (3.3);7.2902 (2.5); 7.2865 (2.4); 7.2828 (1.6); 7.2781 (1.1); 7.2747 (1.4);7.2713 (1.7); 7.2583 (44.3); 7.1235 (1.1); 7.1213 (1.3); 7.1169 (1.4);7.1137 (3.9); 7.1078 (1.6); 7.1018 (4.8); 7.0962 (4.0); 7.0934 (3.0);7.0907 (5.2); 7.0847 (1.9); 7.0788 (5.5); 7.0749 (1.4); 7.0724 (1.2);7.0168 (2.0); 7.0130 (2.7); 7.0105 (2.3); 7.0035 (1.0); 6.9951 (7.2);6.9913 (4.3); 6.9846 (2.2); 6.9816 (1.7); 6.9778 (2.1); 6.9749 (5.7);6.9724 (4.3); 6.9690 (3.0); 6.9640 (2.1); 6.9624 (1.9); 6.9580 (2.4);6.9521 (3.5); 6.9438 (0.6); 6.9008 (0.9); 5.2962 (6.9); 4.8965 (16.0);4.5951 (6.8); 4.5802 (6.7); 1.5591 (3.8); 0.0079 (0.7); −0.0002 (17.1);−0.0085 (0.6) III-011: ¹H-NMR(400.0MHz, CDCl3): δ = 7.3826 (0.7); 7.3676(1.1); 7.3620 (1.6); 7.3474 (1.7); 7.3420 (1.2); 7.3275 (1.3); 7.2605(46.3); 7.1299 (3.6); 7.1245 (2.0); 7.1181 (3.3); 7.1127 (2.4); 7.1102(2.2); 7.1073 (5.9); 7.1043 (2.1); 7.1013 (3.0); 7.0953 (4.4); 7.0891(0.9); 7.0868 (1.2); 7.0827 (0.9); 7.0803 (0.8); 7.0312 (1.7); 7.0275(2.5); 7.0249 (2.0); 7.0085 (4.0); 7.0059 (3.4); 7.0022 (1.9); 6.9979(5.1); 6.9920 (1.5); 6.9859 (2.1); 6.9775 (5.5); 6.9720 (1.6); 6.9606(1.1); 6.9548 (3.2); 6.6633 (0.8); 5.2982 (4.4); 4.8063 (16.0); 2.8459(0.6); 2.8373 (1.0); 2.8280 (1.4); 2.8194 (1.4); 2.8101 (1.1); 2.8014(0.6); 1.5620 (3.0); 1.4319 (0.5); 0.8758 (1.0); 0.8616 (2.6); 0.8583(4.0); 0.8554 (1.9); 0.8445 (3.6); 0.8405 (3.0); 0.8375 (1.7); 0.8270(1.3); 0.6308 (1.3); 0.6208 (2.6); 0.6176 (2.9); 0.6139 (2.8); 0.6119(2.8); 0.6080 (2.9); 0.6044 (2.6); 0.5906 (0.9); 0.0079 (0.5); −0.0002(18.7); −0.0085 (0.6) III-012: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3866(0.9); 7.3850 (0.8); 7.3719 (1.3); 7.3681 (1.2); 7.3660 (1.7); 7.3515(1.9); 7.3467 (1.4); 7.3317 (1.4); 7.2603 (53.4); 7.1415 (3.5); 7.1356(1.8); 7.1344 (1.7); 7.1296 (4.2); 7.1245 (3.1); 7.1186 (5.0); 7.1128(3.3); 7.1103 (3.1); 7.1068 (6.2); 7.0984 (0.9); 7.0919 (1.0); 7.0895(1.0); 7.0854 (1.0); 7.0830 (1.0); 7.0406 (2.0); 7.0380 (2.5); 7.0369(2.8); 7.0343 (2.3); 7.0180 (4.3); 7.0154 (3.4); 7.0129 (2.0); 7.0080(1.5); 6.9994 (5.2); 6.9960 (2.5); 6.9935 (2.4); 6.9895 (2.0); 6.9856(1.7); 6.9821 (2.1); 6.9792 (5.6); 6.9767 (4.3); 6.9734 (1.8); 6.9681(0.7); 6.9621 (1.4); 6.9563 (3.5); 6.7201 (0.8); 5.2981 (2.3); 4.8349(16.0); 4.8229 (0.6); 3.2716 (3.6); 3.2573 (4.2); 3.2540 (4.2); 3.2398(3.7); 1.5602 (3.2); 1.0563 (0.8); 1.0542 (0.8); 1.0484 (0.8); 1.0443(0.6); 1.0364 (1.5); 1.0284 (0.6); 1.0242 (0.8); 1.0184 (0.8); 1.0164(1.0); 1.0043 (0.5); 0.5677 (1.3); 0.5559 (3.2); 0.5529 (3.8); 0.5506(2.2); 0.5478 (1.7); 0.5414 (1.8); 0.5357 (3.7); 0.5328 (3.1); 0.5214(1.6); 0.2840 (1.5); 0.2724 (4.2); 0.2701 (3.6); 0.2604 (3.4); 0.2577(4.3); 0.2460 (1.1); 0.0080 (0.8); −0.0002 (21.5); −0.0085 (0.8)III-013: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3687 (0.6); 7.3631 (0.8);7.3487 (0.9); 7.3433 (0.7); 7.3286 (0.7); 7.2601 (18.6); 7.1347 (1.6);7.1293 (1.1); 7.1229 (2.1); 7.1176 (1.2); 7.1120 (2.6); 7.1080 (1.1);7.1042 (1.3); 7.1004 (2.6); 7.0344 (0.8); 7.0309 (1.3); 7.0282 (1.0);7.0117 (2.0); 7.0094 (1.6); 7.0051 (1.1); 7.0018 (0.6); 6.9966 (2.4);6.9885 (1.0); 6.9845 (1.0); 6.9820 (0.9); 6.9764 (2.8); 6.9711 (0.8);6.9595 (0.5); 6.9538 (1.6); 5.2975 (1.5); 4.8347 (8.3); 3.2365 (2.0);3.2203 (3.3); 3.2044 (2.0); 1.8734 (0.8); 1.8566 (1.1); 1.8398 (0.9);1.5647 (1.4); 0.9700 (16.0); 0.9532 (15.4); −0.0002 (7.2) III-014:¹H-NMR(400.0 MHz, CDCl3): δ = 7.5184 (1.4); 7.3726 (0.6); 7.3626 (0.6);7.3480 (0.7); 7.3418 (0.9); 7.3281 (1.1); 7.3226 (1.0); 7.3076 (1.0);7.2868 (1.1); 7.2595 (250.5); 7.2092 (0.9); 7.1048 (1.2); 7.0983 (1.3);7.0942 (1.2); 7.0832 (1.6); 7.0795 (1.4); 7.0770 (1.6); 7.0320 (1.0);7.0127 (1.0); 6.9955 (2.0); 6.9731 (2.0); 6.9525 (2.0); 6.9303 (1.1);5.2653 (0.6); 5.1635 (0.6); 5.0152 (2.3); 4.9941 (2.0); 4.0569 (0.8);4.0424 (0.8); 3.9668 (0.7); 3.9543 (0.7); 3.0239 (3.7); 2.9833 (3.3);1.5331 (16.0); 0.0080 (4.1); −0.0002 (102.1); −0.0085 (3.9) III-015:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3800 (1.3); 7.3652 (1.2); 7.3594 (2.4);7.3447 (2.0); 7.3388 (1.7); 7.3250 (1.4); 7.2599 (47.4); 7.1604 (0.5);7.1521 (3.4); 7.1463 (1.5); 7.1402 (3.7); 7.1347 (2.5); 7.1292 (5.3);7.1233 (2.5); 7.1212 (2.3); 7.1173 (4.7); 7.1091 (2.2); 7.1066 (2.1);7.1028 (1.9); 7.1002 (2.0); 7.0880 (1.0); 7.0855 (1.0); 7.0816 (1.1);7.0791 (1.0); 7.0431 (1.8); 7.0393 (3.0); 7.0367 (2.6); 7.0325 (2.1);7.0284 (2.3); 7.0262 (2.1); 7.0221 (3.5); 7.0203 (3.8); 7.0175 (1.9);7.0118 (5.2); 7.0058 (2.8); 7.0029 (2.1); 6.9992 (1.8); 6.9946 (2.1);6.9916 (5.5); 6.9890 (4.2); 6.9859 (1.8); 6.9805 (0.8); 6.9745 (1.4);6.9687 (3.4); 6.6717 (0.7); 5.9486 (0.6); 5.9349 (1.3); 5.9227 (0.8);5.9213 (0.8); 5.9091 (1.5); 5.9057 (0.8); 5.8954 (0.8); 5.8920 (1.6);5.8798 (1.0); 5.8784 (0.9); 5.8662 (1.6); 5.8525 (0.8); 5.2975 (1.8);5.2763 (1.0); 5.2720 (2.2); 5.2688 (2.3); 5.2645 (1.0); 5.2333 (0.9);5.2291 (1.9); 5.2259 (2.0); 5.2216 (1.0); 5.1912 (1.1); 5.1876 (2.5);5.1842 (2.4); 5.1807 (1.0); 5.1655 (1.0); 5.1618 (2.3); 5.1585 (2.3);5.1549 (0.9); 4.8668 (16.0); 4.0373 (1.4); 4.0334 (2.4); 4.0294 (1.6);4.0226 (2.6); 4.0191 (4.1); 4.0155 (2.5); 4.0088 (1.6); 4.0048 (2.3);4.0009 (1.4); 1.5587 (2.9); 0.0079 (0.7); −0.0002 (19.0); −0.0085 (0.8)III-016: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3818 (1.1); 7.3668 (1.0);7.3613 (2.2); 7.3464 (1.9); 7.3406 (1.5); 7.3267 (1.3); 7.2600 (35.0);7.1544 (3.1); 7.1487 (1.2); 7.1425 (3.3); 7.1372 (2.1); 7.1317 (5.0);7.1256 (2.3); 7.1233 (2.0); 7.1198 (4.4); 7.1111 (1.8); 7.1085 (1.7);7.1046 (1.6); 7.1023 (1.8); 7.0900 (0.8); 7.0875 (0.8); 7.0835 (0.9);7.0811 (0.8); 7.0453 (1.5); 7.0417 (2.7); 7.0391 (2.2); 7.0341 (1.6);7.0300 (1.9); 7.0233 (3.6); 7.0201 (1.9); 7.0115 (5.3); 7.0058 (2.5);7.0001 (1.6); 6.9944 (1.6); 6.9913 (5.0); 6.9858 (1.5); 6.9743 (1.1);6.9687 (3.2); 6.7735 (0.7); 5.2975 (6.7); 4.9274 (0.8); 4.8645 (16.0);4.1932 (4.3); 4.1868 (4.4); 4.1795 (4.3); 4.1731 (4.2); 3.8121 (1.4);2.2781 (2.6); 2.2717 (5.4); 2.2652 (2.6); 1.5585 (2.7); −0.0002 (13.7)III-017: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3821 (0.8); 7.3672 (0.7);7.3615 (1.5); 7.3470 (1.3); 7.3409 (1.1); 7.3272 (0.9); 7.2606 (19.7);7.1540 (2.2); 7.1482 (0.9); 7.1421 (2.4); 7.1366 (1.6); 7.1311 (3.5);7.1252 (1.7); 7.1230 (1.5); 7.1192 (3.1); 7.1108 (1.4); 7.1083 (1.3);7.1044 (1.3); 7.1020 (1.3); 7.0898 (0.6); 7.0873 (0.6); 7.0833 (0.7);7.0808 (0.6); 7.0460 (1.1); 7.0423 (2.0); 7.0397 (1.7); 7.0361 (1.4);7.0321 (1.4); 7.0299 (1.2); 7.0260 (2.3); 7.0233 (2.0); 7.0204 (1.2);7.0100 (3.6); 7.0067 (1.4); 7.0056 (1.5); 7.0044 (1.5); 6.9983 (0.8);6.9927 (1.2); 6.9899 (3.6); 6.9874 (2.7); 6.9842 (1.2); 6.9728 (0.9);6.9671 (2.3); 6.7110 (0.5); 5.2974 (16.0); 4.8486 (10.5); 4.1364 (0.8);4.1303 (2.2); 4.1240 (2.6); 4.1171 (2.6); 4.1108 (2.2); 4.1047 (0.8);3.8119 (0.8); 1.8344 (0.7); 1.8294 (6.1); 1.8233 (12.3); 1.8171 (6.0);1.5722 (0.7); −0.0002 (7.9) III-018: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3783 (1.1); 7.3632 (1.0); 7.3578 (2.2); 7.3432 (1.8); 7.3372 (1.4);7.3232 (1.2); 7.2604 (37.6); 7.1450 (3.0); 7.1394 (1.2); 7.1332 (3.2);7.1277 (2.6); 7.1224 (5.1); 7.1162 (1.5); 7.1104 (4.4); 7.1057 (1.8);7.1018 (1.9); 7.0994 (1.7); 7.0870 (0.7); 7.0846 (0.7); 7.0806 (0.8);7.0782 (0.8); 7.0378 (1.4); 7.0342 (2.6); 7.0315 (2.2); 7.0277 (1.7);7.0236 (1.8); 7.0215 (1.6); 7.0177 (3.3); 7.0152 (2.9); 7.0104 (4.8);7.0043 (2.6); 6.9983 (2.0); 6.9933 (2.2); 6.9900 (4.9); 6.9879 (3.9);6.9846 (1.5); 6.9731 (1.0); 6.9674 (3.0); 6.6448 (0.8); 5.2977 (5.6);4.8113 (16.0); 2.8352 (0.6); 2.8265 (1.0); 2.8173 (1.4); 2.8086 (1.4);2.7994 (1.1); 2.7907 (0.6); 1.5653 (4.7); 1.2577 (0.5); 0.8712 (1.0);0.8570 (2.6); 0.8536 (3.8); 0.8508 (1.9); 0.8398 (3.6); 0.8358 (2.9);0.8329 (1.7); 0.8224 (1.2); 0.6268 (1.3); 0.6167 (2.6); 0.6136 (2.9);0.6098 (2.8); 0.6080 (2.8); 0.6040 (2.8); 0.6004 (2.6); 0.5865 (0.9);−0.0002 (14.7) III-019: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3766 (1.0);7.3613 (1.0); 7.3559 (2.0); 7.3413 (1.8); 7.3354 (1.3); 7.3212 (1.2);7.2607 (31.4); 7.1496 (2.8); 7.1442 (1.1); 7.1378 (3.0); 7.1325 (2.0);7.1269 (4.7); 7.1203 (2.1); 7.1152 (4.5); 7.1054 (1.9); 7.1028 (2.0);7.0987 (2.0); 7.0964 (2.2); 7.0842 (1.1); 7.0818 (1.2); 7.0777 (1.1);7.0754 (1.1); 7.0426 (1.3); 7.0391 (2.5); 7.0366 (2.0); 7.0322 (1.5);7.0280 (1.7); 7.0260 (1.5); 7.0204 (2.9); 7.0170 (1.6); 7.0080 (5.2);7.0023 (2.4); 6.9978 (1.2); 6.9875 (4.4); 6.9856 (3.8); 6.9823 (1.4);6.9707 (1.0); 6.9651 (2.9); 5.2977 (6.5); 4.8244 (15.2); 4.1832 (2.2);4.1654 (6.8); 4.1475 (6.9); 4.1296 (2.3); 3.6791 (1.6); 3.6637 (4.0);3.6484 (4.2); 3.6329 (1.6); 2.6151 (3.6); 2.6097 (0.7); 2.5997 (5.7);2.5904 (0.6); 2.5846 (3.4); 1.5715 (2.5); 1.2793 (7.7); 1.2615 (16.0);1.2436 (7.6); −0.0002 (12.3) III-020: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3711 (0.7); 7.3606 (7.3); 7.3572 (3.1); 7.3552 (4.0); 7.3524 (7.7);7.3496 (4.2); 7.3469 (3.4); 7.3442 (7.9); 7.3401 (2.6); 7.3327 (4.3);7.3273 (1.8); 7.3197 (4.2); 7.3153 (2.3); 7.3104 (4.8); 7.3030 (1.9);7.2975 (4.5); 7.2900 (0.7); 7.2635 (33.4); 7.2140 (1.0); 7.2023 (4.3);7.1993 (2.4); 7.1950 (3.0); 7.1921 (2.9); 7.1879 (3.0); 7.1859 (2.7);7.1810 (1.9); 7.1779 (3.3); 7.1229 (0.5); 7.1156 (4.6); 7.1101 (1.4);7.1018 (0.7); 7.0985 (1.5); 7.0943 (6.9); 7.0894 (1.6); 7.0778 (1.2);7.0724 (3.7); 6.5837 (1.0); 5.9140 (0.6); 5.9003 (1.4); 5.8880 (0.9);5.8746 (1.6); 5.8712 (0.9); 5.8608 (0.8); 5.8574 (1.7); 5.8450 (1.0);5.8317 (1.7); 5.8180 (0.8); 5.3784 (1.1); 5.3615 (3.6); 5.3445 (3.6);5.3275 (1.2); 5.2342 (1.0); 5.2301 (2.3); 5.2267 (2.6); 5.2226 (1.1);5.1913 (0.9); 5.1872 (2.1); 5.1838 (2.2); 5.1797 (0.9); 5.1691 (1.0);5.1656 (2.7); 5.1622 (2.6); 5.1588 (1.0); 5.1435 (1.0); 5.1399 (2.5);5.1365 (2.5); 5.1331 (1.0); 3.9879 (1.5); 3.9840 (2.7); 3.9801 (1.7);3.9734 (2.8); 3.9697 (4.8); 3.9660 (2.9); 3.9593 (1.7); 3.9554 (2.7);3.9515 (1.6); 1.7097 (15.9); 1.6927 (16.0); 1.6645 (0.8); 1.6476 (0.8);1.4323 (2.7); 0.9952 (0.5); 0.9913 (0.6); −0.0002 (14.3) III-021:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3629 (0.7); 7.3570 (3.0); 7.3543 (1.5);7.3485 (3.3); 7.3439 (1.9); 7.3406 (3.8); 7.3363 (2.7); 7.3305 (1.2);7.3231 (1.9); 7.3187 (1.2); 7.3137 (2.2); 7.3063 (1.0); 7.3009 (2.1);7.2639 (20.6); 7.2003 (2.0); 7.1976 (1.1); 7.1917 (1.6); 7.1863 (1.3);7.1832 (1.3); 7.1791 (0.9); 7.1759 (1.5); 7.1121 (2.0); 7.1067 (0.7);7.0950 (0.8); 7.0908 (3.0); 7.0858 (0.9); 7.0742 (0.6); 7.0689 (1.7);5.3017 (4.2); 5.2988 (1.8); 5.2816 (1.6); 3.6867 (16.0); 3.6294 (0.8);3.6247 (1.2); 3.6099 (1.7); 3.5953 (1.3); 2.5996 (1.8); 2.5843 (3.2);2.5689 (1.6); 1.6809 (6.5); 1.6730 (0.8); 1.6639 (6.4); 1.6561 (0.6);1.4323 (1.4); −0.0002 (8.3) III-022: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3810 (1.2); 7.3662 (1.0); 7.3604 (2.3); 7.3457 (1.9); 7.3398 (1.6);7.3261 (1.3); 7.2605 (37.7); 7.1610 (3.3); 7.1552 (1.2); 7.1491 (3.5);7.1437 (2.2); 7.1381 (4.7); 7.1320 (1.5); 7.1262 (5.1); 7.1218 (1.1);7.1191 (1.2); 7.1069 (1.5); 7.1044 (1.6); 7.1006 (1.6); 7.0981 (1.7);7.0858 (0.7); 7.0834 (0.8); 7.0794 (0.8); 7.0769 (0.8); 7.0411 (1.6);7.0374 (2.8); 7.0347 (2.4); 7.0306 (2.0); 7.0266 (2.2); 7.0243 (1.8);7.0204 (7.5); 7.0148 (2.3); 7.0068 (1.8); 7.0031 (2.7); 7.0001 (6.3);6.9974 (4.8); 6.9945 (1.7); 6.9830 (1.2); 6.9773 (3.3); 6.6686 (0.6);5.9450 (0.6); 5.9312 (1.3); 5.9191 (0.8); 5.9176 (0.8); 5.9055 (1.5);5.9021 (0.8); 5.8917 (0.8); 5.8883 (1.6); 5.8762 (0.9); 5.8746 (0.9);5.8626 (1.6); 5.8488 (0.8); 5.2978 (10.2); 5.2728 (0.9); 5.2686 (2.1);5.2653 (2.3); 5.2611 (1.0); 5.2299 (0.8); 5.2257 (1.9); 5.2224 (2.0);5.2181 (0.9); 5.1903 (0.9); 5.1867 (2.5); 5.1833 (2.4); 5.1797 (0.9);5.1645 (0.9); 5.1610 (2.3); 5.1576 (2.2); 5.1540 (0.8); 4.8669 (16.0);4.0364 (1.2); 4.0324 (2.2); 4.0285 (1.4); 4.0218 (2.2); 4.0181 (3.8);4.0144 (2.2); 4.0077 (1.3); 4.0038 (2.1); 3.9999 (1.2); 1.5879 (1.1);1.4318 (0.9); −0.0002 (15.2) III-023: ¹H-NMR(400.0 MHz, CDCl3): δ =7.3623 (0.7); 7.3475 (0.6); 7.2605 (10.0); 7.1634 (1.0); 7.1516 (1.0);7.1462 (0.7); 7.1407 (1.4); 7.1289 (1.5); 7.1000 (0.5); 7.0396 (0.8);7.0370 (0.7); 7.0320 (0.6); 7.0280 (0.7); 7.0204 (2.3); 7.0083 (0.7);7.0000 (1.8); 6.9773 (1.0); 5.2980 (16.0); 4.8645 (5.0); 4.1933 (1.4);4.1869 (1.4); 4.1796 (1.4); 4.1732 (1.3); 2.2780 (0.9); 2.2716 (1.9);2.2652 (0.9); 1.5728 (0.5); −0.0002 (4.1) III-024: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3795 (0.5); 7.3589 (1.0); 7.3443 (0.8); 7.3383 (0.7);7.3243 (0.6); 7.2610 (17.9); 7.1541 (1.4); 7.1485 (0.5); 7.1423 (1.5);7.1369 (1.0); 7.1313 (2.1); 7.1250 (1.0); 7.1194 (2.2); 7.1060 (0.7);7.1035 (0.7); 7.0996 (0.7); 7.0972 (0.7); 7.0358 (0.7); 7.0320 (1.2);7.0294 (1.1); 7.0259 (0.9); 7.0215 (1.1); 7.0191 (2.6); 7.0157 (1.6);7.0131 (1.8); 7.0018 (1.3); 6.9986 (2.7); 6.9963 (2.3); 6.9928 (1.0);6.9760 (1.4); 5.2982 (16.0); 4.8113 (7.1); 2.8143 (0.6); 2.8058 (0.6);1.5740 (1.3); 0.8564 (1.1); 0.8532 (1.7); 0.8502 (0.8); 0.8393 (1.6);0.8353 (1.3); 0.8323 (0.7); 0.8218 (0.6); 0.6289 (0.6); 0.6189 (1.2);0.6158 (1.3); 0.6120 (1.2); 0.6100 (1.2); 0.6061 (1.3); 0.6026 (1.1);−0.0002 (7.2) III-025: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3833 (1.2);7.3685 (1.0); 7.3628 (2.3); 7.3482 (1.9); 7.3422 (1.6); 7.3283 (1.3);7.2608 (36.5); 7.1653 (3.3); 7.1596 (1.2); 7.1534 (3.5); 7.1480 (2.2);7.1425 (4.7); 7.1364 (1.5); 7.1306 (5.0); 7.1275 (1.3); 7.1234 (1.2);7.1212 (1.2); 7.1087 (1.5); 7.1062 (1.7); 7.1023 (1.6); 7.0998 (1.8);7.0876 (0.8); 7.0851 (0.8); 7.0811 (0.8); 7.0787 (0.8); 7.0451 (1.5);7.0413 (2.8); 7.0387 (2.4); 7.0357 (2.0); 7.0317 (2.0); 7.0293 (2.0);7.0254 (3.5); 7.0202 (5.9); 7.0141 (1.8); 7.0120 (2.0); 7.0083 (1.9);7.0057 (1.8); 6.9999 (5.5); 6.9975 (4.2); 6.9943 (1.6); 6.9829 (1.2);6.9772 (3.3); 6.6928 (0.7); 5.2979 (16.0); 4.8422 (15.8); 3.2639 (3.5);3.2495 (4.0); 3.2463 (4.0); 3.2320 (3.5); 1.5787 (2.7); 1.0458 (0.8);1.0438 (0.8); 1.0380 (0.7); 1.0339 (0.5); 1.0259 (1.4); 1.0180 (0.6);1.0137 (0.7); 1.0080 (0.8); 1.0060 (0.9); 0.5591 (1.2); 0.5473 (3.0);0.5442 (3.6); 0.5420 (2.0); 0.5392 (1.6); 0.5328 (1.6); 0.5272 (3.4);0.5242 (2.9); 0.5128 (1.4); 0.2732 (1.4); 0.2616 (4.0); 0.2496 (3.1);0.2468 (4.1); 0.2349 (1.0); 0.0701 (0.8); −0.0002 (14.8) III-026:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3791 (0.6); 7.3642 (0.5); 7.3586 (1.1);7.3438 (1.0); 7.3379 (0.8); 7.3241 (0.6); 7.2614 (16.9); 7.1596 (1.6);7.1539 (0.7); 7.1477 (1.8); 7.1423 (1.2); 7.1367 (2.3); 7.1306 (0.9);7.1250 (2.6); 7.1191 (0.8); 7.1166 (1.0); 7.1043 (1.1); 7.1018 (1.2);7.0979 (1.2); 7.0955 (1.3); 7.0832 (0.7); 7.0808 (0.7); 7.0768 (0.7);7.0744 (0.6); 7.0429 (0.8); 7.0392 (1.4); 7.0366 (1.2); 7.0323 (1.0);7.0282 (1.1); 7.0261 (1.2); 7.0179 (2.9); 7.0120 (0.9); 7.0083 (1.0);7.0053 (1.0); 7.0010 (1.3); 6.9977 (3.1); 6.9920 (0.9); 6.9806 (0.7);6.9749 (1.6); 5.2983 (4.1); 4.8241 (8.1); 3.6958 (16.0); 3.6787 (1.0);3.6633 (2.3); 3.6480 (2.3); 3.6325 (1.0); 2.6318 (1.9); 2.6164 (2.9);2.6012 (1.8); 1.5819 (2.0); −0.0002 (6.8) III-027: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3797 (0.6); 7.3649 (0.6); 7.3592 (1.1); 7.3444 (0.9);7.3383 (0.6); 7.3246 (0.6); 7.2609 (19.2); 7.1705 (1.7); 7.1649 (0.6);7.1587 (1.8); 7.1533 (1.1); 7.1477 (2.3); 7.1416 (0.8); 7.1359 (2.2);7.1256 (0.6); 7.1230 (0.6); 7.1191 (0.6); 7.1166 (0.7); 7.1044 (1.1);7.1017 (1.2); 7.0983 (1.0); 7.0955 (1.2); 7.0833 (0.6); 7.0808 (0.5);7.0768 (0.5); 7.0469 (0.8); 7.0431 (1.3); 7.0405 (1.1); 7.0333 (0.8);7.0291 (1.3); 7.0270 (1.6); 7.0235 (2.4); 7.0200 (2.6); 7.0141 (0.8);7.0091 (1.0); 7.0028 (1.4); 6.9996 (3.0); 6.9940 (0.8); 6.9826 (0.6);6.9769 (1.6); 5.2981 (4.6); 4.8950 (7.8); 4.1775 (3.6); 4.1639 (3.6);3.7892 (16.0); 1.5695 (2.2); −0.0002 (7.7) III-028: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.5194 (0.7); 7.5156 (0.9); 7.5127 (1.1); 7.5093 (0.7);7.5007 (0.8); 7.4942 (2.9); 7.4881 (1.0); 7.4791 (1.5); 7.4756 (2.8);7.4721 (1.5); 7.4514 (0.7); 7.4461 (3.2); 7.4427 (1.7); 7.4310 (2.9);7.4272 (5.7); 7.4227 (1.6); 7.4137 (1.1); 7.4093 (3.0); 7.4061 (1.8);7.3639 (0.7); 7.3593 (0.7); 7.3463 (0.7); 7.3412 (0.6); 7.3308 (0.9);7.3257 (4.6); 7.3226 (5.6); 7.3189 (2.7); 7.3104 (1.4); 7.3053 (5.0);7.3015 (3.4); 7.2606 (65.6); 7.2496 (1.7); 7.2484 (1.7); 7.2438 (3.0);7.2287 (2.4); 7.2234 (1.9); 7.2092 (1.2); 7.2077 (1.2); 7.0346 (1.1);7.0324 (1.3); 7.0283 (1.5); 7.0261 (1.5); 7.0138 (2.4); 7.0115 (2.7);7.0074 (2.6); 7.0056 (2.7); 6.9966 (1.1); 6.9932 (1.2); 6.9910 (1.2);6.9870 (1.2); 6.9847 (1.1); 6.9403 (1.4); 6.9350 (2.2); 6.9293 (1.5);6.9168 (1.2); 6.9117 (2.0); 6.9072 (3.6); 6.9052 (3.7); 6.9023 (1.6);6.8998 (1.4); 6.8869 (1.7); 6.8855 (1.8); 6.8821 (1.4); 5.9884 (0.9);5.2981 (10.6); 4.9142 (1.7); 4.9026 (16.0); 4.7268 (1.1); 2.8681 (0.7);2.8592 (1.2); 2.8501 (1.6); 2.8411 (1.6); 2.8320 (1.2); 2.8231 (0.8);2.0433 (0.6); 1.5631 (4.3); 1.2584 (0.6); 0.8814 (1.2); 0.8757 (0.6);0.8669 (2.6); 0.8640 (4.2); 0.8610 (2.3); 0.8501 (3.8); 0.8461 (3.1);0.8430 (2.0); 0.8370 (0.7); 0.8326 (1.6); 0.6537 (1.4); 0.6438 (3.0);0.6405 (3.3); 0.6349 (3.2); 0.6309 (3.3); 0.6272 (2.9); 0.6134 (1.3);0.0079 (0.8); −0.0002 (26.2); −0.0085 (1.0) III-029: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.5124 (0.5); 7.5090 (0.5); 7.4907 (1.4); 7.4845 (0.5);7.4757 (0.8); 7.4722 (1.4); 7.4686 (0.8); 7.4446 (1.6); 7.4411 (0.9);7.4296 (1.5); 7.4258 (2.9); 7.4212 (0.8); 7.4123 (0.8); 7.4078 (1.8);7.4045 (1.2); 7.3558 (0.6); 7.3402 (0.6); 7.3349 (2.3); 7.3318 (2.8);7.3281 (1.3); 7.3196 (0.8); 7.3145 (2.4); 7.3107 (1.7); 7.2610 (20.9);7.2555 (0.7); 7.2513 (0.6); 7.2485 (0.8); 7.2428 (1.3); 7.2276 (1.2);7.2222 (0.9); 7.2072 (0.7); 7.0340 (0.6); 7.0319 (0.6); 7.0278 (0.6);7.0257 (0.6); 7.0135 (0.8); 7.0112 (0.9); 7.0072 (1.0); 7.0050 (0.9);6.9865 (0.5); 6.9610 (0.7); 6.9556 (1.1); 6.9500 (0.6); 6.9375 (0.7);6.9323 (1.0); 6.9267 (0.7); 6.9137 (0.9); 6.9120 (1.0); 6.9088 (0.8);6.9068 (0.7); 6.8933 (0.8); 6.8920 (0.8); 6.8884 (0.7); 6.8869 (0.6);5.2979 (9.4); 4.9951 (0.9); 4.9831 (7.6); 4.8328 (0.6); 4.1905 (3.8);4.1766 (3.8); 4.1669 (0.5); 3.7927 (16.0); 3.7800 (1.5); −0.0002 (8.5)III-030: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5037 (1.4); 7.5004 (0.8);7.4916 (0.8); 7.4852 (3.0); 7.4792 (1.1); 7.4701 (1.6); 7.4666 (2.9);7.4631 (1.6); 7.4415 (0.8); 7.4363 (3.3); 7.4328 (1.8); 7.4212 (3.1);7.4174 (5.8); 7.4129 (1.6); 7.4038 (1.2); 7.3994 (3.2); 7.3962 (1.9);7.3448 (10.8); 7.3442 (10.8); 7.3378 (5.2); 7.3331 (13.0); 7.3248 (2.0);7.3177 (2.1); 7.3139 (2.4); 7.3089 (6.3); 7.3058 (6.6); 7.3006 (5.1);7.2933 (3.0); 7.2884 (6.5); 7.2847 (4.7); 7.2792 (2.8); 7.2737 (1.6);7.2684 (1.9); 7.2587 (55.0); 7.2478 (2.6); 7.2420 (3.7); 7.2326 (1.7);7.2269 (3.1); 7.2216 (2.2); 7.2134 (1.0); 7.2070 (1.7); 7.1927 (0.5);7.0357 (0.9); 7.0334 (1.0); 7.0294 (1.0); 7.0272 (1.0); 7.0150 (1.7);7.0127 (1.9); 7.0088 (1.7); 7.0066 (1.8); 6.9943 (1.3); 6.9921 (1.1);6.9880 (1.1); 6.9858 (1.0); 6.9451 (0.6); 6.9345 (1.3); 6.9290 (2.2);6.9235 (1.5); 6.9109 (1.2); 6.9059 (2.1); 6.8988 (2.8); 6.8961 (2.6);6.8932 (1.6); 6.8908 (1.4); 6.8778 (1.8); 6.8764 (1.8); 6.8730 (1.5);6.8712 (1.3); 5.9808 (1.3); 5.2961 (16.0); 4.9904 (2.1); 4.9819 (15.6);4.8250 (1.6); 4.7655 (0.6); 4.6005 (7.1); 4.5854 (7.0); 4.5689 (0.9);4.5540 (0.8); 1.5619 (3.4); 0.0080 (0.8); −0.0002 (22.3); −0.0085 (0.8)III-031: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5362 (0.6); 7.5167 (1.4);7.5132 (1.2); 7.5098 (0.7); 7.5013 (0.8); 7.4988 (0.7); 7.4948 (3.0);7.4887 (1.1); 7.4797 (1.6); 7.4762 (2.9); 7.4727 (1.6); 7.4529 (0.7);7.4490 (2.8); 7.4476 (3.2); 7.4441 (1.8); 7.4325 (3.0); 7.4287 (5.9);7.4240 (1.6); 7.4152 (1.2); 7.4108 (3.2); 7.4076 (1.9); 7.3713 (0.9);7.3681 (1.0); 7.3647 (0.6); 7.3603 (0.8); 7.3553 (0.7); 7.3508 (1.1);7.3469 (0.9); 7.3421 (0.8); 7.3353 (0.9); 7.3302 (4.8); 7.3271 (5.9);7.3248 (2.6); 7.3233 (2.9); 7.3148 (1.5); 7.3097 (5.1); 7.3060 (3.6);7.2665 (2.1); 7.2600 (90.9); 7.2520 (2.8); 7.2462 (3.2); 7.2350 (1.1);7.2310 (2.6); 7.2256 (1.8); 7.2201 (0.6); 7.2153 (0.8); 7.2110 (1.6);7.2012 (0.7); 7.0368 (1.4); 7.0346 (1.6); 7.0305 (1.6); 7.0283 (1.7);7.0159 (2.4); 7.0138 (2.7); 7.0098 (2.6); 7.0077 (2.5); 6.9957 (1.8);6.9932 (1.3); 6.9892 (1.4); 6.9869 (1.4); 6.9497 (1.4); 6.9444 (2.4);6.9390 (1.6); 6.9263 (1.3); 6.9213 (2.2); 6.9141 (2.8); 6.9115 (2.6);6.9085 (1.6); 6.9062 (1.4); 6.8932 (1.6); 6.8918 (1.7); 6.8884 (1.4);6.0755 (0.5); 6.0122 (1.0); 5.9580 (0.7); 5.9441 (1.5); 5.9321 (0.9);5.9304 (0.9); 5.9184 (1.7); 5.9151 (1.0); 5.9045 (1.0); 5.9012 (1.9);5.8892 (1.1); 5.8875 (1.2); 5.8754 (1.9); 5.8616 (0.9); 5.3045 (1.0);5.3003 (2.5); 5.2978 (3.5); 5.2931 (1.2); 5.2615 (1.0); 5.2573 (2.2);5.2543 (2.3); 5.2501 (1.2); 5.2208 (0.5); 5.2154 (1.2); 5.2119 (2.6);5.2087 (2.6); 5.2052 (1.2); 5.1950 (0.5); 5.1897 (1.1); 5.1862 (2.4);5.1830 (2.3); 5.1795 (1.0); 5.1735 (0.5); 4.9628 (2.6); 4.9512 (16.0);4.7881 (1.8); 4.7298 (0.6); 4.0499 (1.6); 4.0459 (2.4); 4.0418 (1.8);4.0357 (3.0); 4.0317 (4.5); 4.0278 (2.7); 4.0214 (1.9); 4.0174 (2.6);4.0136 (1.6); 4.0008 (0.7); 1.5559 (5.7); 0.0080 (1.2); −0.0002 (38.0);−0.0085 (1.4) III-035: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4378 (0.8);7.4325 (1.4); 7.4250 (6.7); 7.4212 (7.1); 7.4150 (2.8); 7.4111 (2.5);7.4069 (4.4); 7.4053 (3.9); 7.3981 (1.3); 7.3939 (1.5); 7.3879 (0.6);7.3836 (0.7); 7.3186 (0.6); 7.3113 (4.7); 7.3071 (5.2); 7.3020 (2.0);7.3002 (1.9); 7.2976 (1.8); 7.2948 (2.4); 7.2925 (2.6); 7.2871 (3.5);7.2601 (36.3); 7.2271 (1.0); 7.2109 (1.0); 7.2067 (2.1); 7.1919 (1.7);7.1905 (1.8); 7.1874 (1.3); 7.1724 (1.0); 7.1705 (1.0); 6.9607 (0.8);6.9554 (2.0); 6.9506 (1.8); 6.9473 (1.5); 6.9447 (1.7); 6.9409 (0.8);6.9380 (0.9); 6.9362 (0.9); 6.9309 (2.0); 6.9268 (3.7); 6.9241 (3.9);6.9202 (1.7); 6.9175 (3.5); 6.9145 (2.3); 6.9101 (1.5); 6.9060 (1.1);6.9037 (1.4); 6.8974 (2.5); 6.8951 (1.8); 6.8924 (1.7); 6.8901 (1.3);6.7097 (0.7); 5.2973 (7.6); 4.8608 (16.0); 3.2684 (3.6); 3.2541 (4.2);3.2509 (4.2); 3.2366 (3.6); 1.5736 (3.6); 1.0504 (0.8); 1.0484 (0.8);1.0425 (0.7); 1.0385 (0.6); 1.0361 (0.5); 1.0305 (1.4); 1.0225 (0.6);1.0183 (0.8); 1.0125 (0.8); 1.0105 (0.9); 0.5610 (1.2); 0.5491 (3.2);0.5462 (3.7); 0.5440 (2.3); 0.5411 (1.7); 0.5347 (1.8); 0.5291 (3.6);0.5261 (3.1); 0.5147 (1.4); 0.2767 (1.4); 0.2651 (4.2); 0.2531 (3.4);0.2503 (4.3); 0.2384 (1.0); −0.0002 (14.4); −0.0084 (0.6) III-038:¹H-NMR(400.0 MHz, CDCl3): δ = 8.9430 (1.5); 7.4486 (0.7); 7.4444 (0.8);7.4322 (3.8); 7.4281 (4.7); 7.4193 (7.5); 7.4170 (12.4); 7.4148 (14.1);7.4095 (9.7); 7.4031 (4.9); 7.3991 (6.9); 7.3974 (6.3); 7.3891 (2.5);7.3852 (3.2); 7.3742 (4.3); 7.3655 (7.3); 7.3573 (3.9); 7.3514 (7.5);7.3478 (6.9); 7.3404 (1.8); 7.2726 (1.2); 7.2655 (6.8); 7.2609 (10.1);7.2581 (49.7); 7.2517 (3.4); 7.2484 (4.1); 7.2466 (4.4); 7.2415 (5.0);7.2110 (1.1); 7.1904 (2.2); 7.1746 (2.2); 7.1702 (1.6); 7.1541 (1.2);6.9328 (1.1); 6.9286 (1.4); 6.9267 (1.5); 6.9060 (3.6); 6.9000 (2.0);6.8939 (1.7); 6.8875 (1.8); 6.8854 (1.8); 6.8754 (1.9); 6.8655 (3.0);6.8639 (2.9); 6.8450 (2.1); 6.8412 (2.1); 5.2951 (16.0); 4.9969 (13.2);4.9029 (5.9); 4.7024 (2.2); 1.5851 (0.9); 0.0079 (0.6); −0.0002 (20.3);−0.0085 (0.8) III-039: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.4141 (1.2);7.3996 (1.1); 7.3936 (2.4); 7.3790 (1.9); 7.3728 (1.7); 7.3593 (1.4);7.2611 (47.7); 7.2040 (1.0); 7.2015 (1.1); 7.1977 (1.1); 7.1952 (1.1);7.1829 (1.8); 7.1803 (2.0); 7.1767 (1.9); 7.1740 (2.0); 7.1624 (4.1);7.1594 (1.8); 7.1567 (1.8); 7.1509 (3.9); 7.1453 (2.6); 7.1397 (5.2);7.1338 (1.7); 7.1280 (5.0); 7.1197 (0.6); 7.0759 (1.8); 7.0721 (3.0);7.0695 (2.6); 7.0641 (1.9); 7.0600 (2.3); 7.0560 (2.6); 7.0535 (4.3);7.0412 (2.0); 7.0357 (6.6); 7.0302 (2.3); 7.0242 (0.9); 7.0158 (5.6);7.0129 (4.2); 7.0102 (1.9); 7.0045 (0.6); 6.9987 (1.3); 6.9930 (3.6);6.9289 (0.9); 5.2984 (1.2); 5.0248 (0.5); 4.8993 (16.0); 3.8220 (1.0);3.4083 (1.8); 3.3907 (3.3); 3.3756 (3.3); 3.3577 (1.8); 1.6204 (1.7);1.6028 (2.6); 1.5955 (1.5); 1.5844 (2.4); 1.5740 (2.6); 1.3826 (1.5);1.3733 (3.8); 1.3644 (5.3); 1.3549 (6.6); 1.3460 (3.1); 1.3372 (1.7);0.9288 (3.6); 0.9244 (2.1); 0.9113 (11.0); 0.9052 (2.4); 0.8971 (2.0);0.8934 (3.0); 0.0080 (0.6); −0.0002 (19.1); −0.0085 (0.7) III-040:¹H-NMR(400.0 MHz, CDCl3): δ = 7.4161 (1.3); 7.4017 (1.1); 7.3956 (2.4);7.3908 (0.5); 7.3811 (1.9); 7.3747 (1.7); 7.3615 (1.4); 7.2611 (46.2);7.2054 (1.0); 7.2029 (1.1); 7.1990 (1.1); 7.1965 (1.2); 7.1843 (1.8);7.1816 (1.9); 7.1781 (1.8); 7.1754 (2.2); 7.1666 (3.7); 7.1632 (1.8);7.1608 (2.3); 7.1549 (4.4); 7.1494 (2.8); 7.1437 (5.2); 7.1378 (1.8);7.1320 (4.9); 7.1237 (0.8); 7.0801 (2.0); 7.0762 (3.2); 7.0737 (2.9);7.0678 (2.4); 7.0638 (3.0); 7.0602 (3.3); 7.0574 (5.3); 7.0455 (2.9);7.0375 (6.6); 7.0316 (2.3); 7.0259 (1.2); 7.0200 (2.2); 7.0176 (5.8);7.0145 (4.3); 7.0118 (2.1); 7.0061 (0.8); 7.0004 (1.5); 6.9947 (3.6);6.9863 (0.5); 5.2985 (3.1); 4.9118 (16.0); 3.2784 (3.6); 3.2642 (4.2);3.2607 (4.4); 3.2466 (3.8); 1.5731 (2.4); 1.0671 (0.8); 1.0651 (0.8);1.0592 (0.8); 1.0551 (0.6); 1.0528 (0.6); 1.0472 (1.6); 1.0392 (0.7);1.0350 (0.8); 1.0292 (0.9); 1.0272 (1.0); 1.0151 (0.6); 0.5872 (1.2);0.5753 (3.2); 0.5724 (4.0); 0.5700 (2.4); 0.5673 (1.8); 0.5608 (2.0);0.5552 (3.8); 0.5523 (3.3); 0.5408 (1.7); 0.2972 (1.4); 0.2855 (4.3);0.2832 (3.7); 0.2735 (3.5); 0.2708 (4.5); 0.2590 (1.3); 0.0080 (0.6);−0.0002 (19.7); −0.0084 (0.9) III-041: ¹H-NMR(400.0 MHz, CDCl3): δ =7.4129 (1.2); 7.3984 (1.1); 7.3923 (2.3); 7.3778 (1.8); 7.3715 (1.6);7.3582 (1.3); 7.2610 (53.3); 7.2035 (0.9); 7.2009 (1.1); 7.1972 (1.0);7.1946 (1.1); 7.1824 (1.7); 7.1798 (1.8); 7.1762 (1.7); 7.1735 (1.8);7.1611 (1.1); 7.1569 (3.5); 7.1513 (1.7); 7.1452 (3.5); 7.1397 (2.4);7.1339 (4.8); 7.1281 (1.6); 7.1256 (1.4); 7.1223 (4.7); 7.1140 (0.6);7.0721 (1.8); 7.0683 (2.9); 7.0657 (2.5); 7.0601 (1.9); 7.0561 (2.3);7.0522 (2.6); 7.0496 (4.2); 7.0439 (1.1); 7.0355 (5.6); 7.0301 (2.4);7.0278 (1.6); 7.0240 (1.0); 7.0181 (2.1); 7.0156 (5.5); 7.0126 (4.1);7.0099 (2.1); 7.0041 (1.1); 6.9985 (2.1); 6.9927 (4.2); 6.9845 (1.0);5.2986 (5.9); 4.8865 (16.0); 2.8649 (0.7); 2.8561 (1.1); 2.8469 (1.5);2.8380 (1.6); 2.8288 (1.1); 2.8200 (0.7); 1.5641 (3.4); 1.2585 (0.5);0.8827 (1.1); 0.8683 (2.8); 0.8654 (4.2); 0.8623 (2.0); 0.8514 (3.8);0.8475 (3.1); 0.8444 (1.8); 0.8338 (1.3); 0.6509 (1.3); 0.6409 (2.9);0.6377 (3.2); 0.6341 (2.9); 0.6319 (3.0); 0.6281 (3.2); 0.6246 (2.7);0.6107 (1.0); 0.0080 (0.7); −0.0002 (22.6); −0.0085 (0.8) III-042:¹H-NMR(400.0 MHz, CDCl3): δ = 7.4159 (1.1); 7.4010 (1.1); 7.3953 (2.2);7.3911 (0.6); 7.3808 (1.8); 7.3744 (1.4); 7.3608 (1.4); 7.2612 (28.4);7.2056 (1.0); 7.2032 (1.1); 7.1992 (1.1); 7.1969 (1.1); 7.1845 (1.7);7.1819 (1.8); 7.1783 (1.8); 7.1757 (1.9); 7.1636 (3.8); 7.1577 (2.0);7.1521 (3.6); 7.1467 (2.5); 7.1410 (4.8); 7.1351 (1.8); 7.1293 (4.8);7.1210 (1.0); 7.0948 (1.1); 7.0788 (2.1); 7.0752 (3.2); 7.0726 (2.6);7.0660 (2.0); 7.0619 (2.4); 7.0592 (3.1); 7.0559 (4.6); 7.0432 (2.1);7.0377 (6.1); 7.0323 (2.3); 7.0263 (1.0); 7.0178 (5.1); 7.0151 (3.9);7.0124 (1.9); 7.0066 (0.7); 7.0008 (1.3); 6.9952 (3.3); 5.2984 (5.3);4.9386 (16.0); 4.2016 (4.4); 4.1953 (4.7); 4.1880 (4.6); 4.1816 (4.5);3.8217 (0.7); 2.2867 (2.5); 2.2803 (5.2); 2.2739 (2.7); 2.0433 (0.6);1.5721 (1.6); −0.0002 (12.3); −0.0085 (0.6) III-043: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.4140 (1.2); 7.3995 (1.1); 7.3935 (2.3); 7.3890 (0.5);7.3790 (1.8); 7.3726 (1.5); 7.3592 (1.3); 7.2613 (35.5); 7.2037 (1.0);7.2011 (1.1); 7.1973 (1.0); 7.1948 (1.1); 7.1826 (1.7); 7.1799 (1.8);7.1764 (1.8); 7.1736 (2.0); 7.1647 (3.5); 7.1615 (1.7); 7.1590 (2.1);7.1529 (4.2); 7.1475 (2.5); 7.1418 (5.0); 7.1359 (1.6); 7.1301 (4.7);7.1219 (0.6); 7.0767 (1.8); 7.0728 (2.8); 7.0703 (2.4); 7.0641 (1.8);7.0600 (2.4); 7.0571 (2.8); 7.0538 (4.8); 7.0462 (1.0); 7.0409 (2.3);7.0379 (6.2); 7.0319 (2.5); 7.0264 (1.1); 7.0181 (5.7); 7.0151 (4.3);7.0124 (2.2); 7.0066 (1.1); 7.0009 (1.9); 6.9952 (4.0); 6.9869 (0.9);5.9558 (0.6); 5.9419 (1.4); 5.9300 (0.8); 5.9282 (0.8); 5.9162 (1.6);5.9128 (0.9); 5.9023 (0.9); 5.8990 (1.6); 5.8870 (0.9); 5.8853 (0.9);5.8732 (1.7); 5.8594 (0.8); 5.3015 (1.3); 5.2981 (7.6); 5.2945 (2.6);5.2903 (1.1); 5.2588 (0.9); 5.2546 (2.0); 5.2515 (2.0); 5.2473 (0.9);5.2154 (1.1); 5.2119 (2.6); 5.2087 (2.4); 5.2052 (1.0); 5.1897 (1.0);5.1861 (2.4); 5.1829 (2.3); 5.1794 (0.9); 4.9349 (16.0); 4.0468 (1.4);4.0431 (2.3); 4.0391 (1.5); 4.0325 (2.7); 4.0288 (4.4); 4.0251 (2.6);4.0185 (1.6); 4.0145 (2.3); 4.0107 (1.3); 1.5850 (1.2); −0.0002 (14.3);−0.0085 (0.6) III-045: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5181 (1.5);7.3032 (1.2); 7.2976 (1.7); 7.2931 (1.2); 7.2831 (7.3); 7.2816 (6.9);7.2777 (4.5); 7.2750 (3.8); 7.2699 (6.4); 7.2592 (256.6); 7.2500 (5.6);7.2477 (5.8); 7.2440 (1.8); 7.2381 (2.3); 7.2365 (2.1); 7.2223 (0.5);7.2187 (0.7); 7.2092 (0.6); 7.1748 (0.6); 7.1471 (4.5); 7.1430 (5.4);7.1373 (1.6); 7.1307 (2.4); 7.1261 (4.4); 7.1227 (3.6); 7.0952 (0.6);7.0881 (4.6); 7.0826 (1.4); 7.0711 (1.7); 7.0666 (6.7); 7.0614 (1.6);7.0499 (1.3); 7.0445 (3.6); 6.9952 (1.4); 6.7413 (0.8); 5.9268 (0.6);5.9133 (1.3); 5.9007 (0.9); 5.8875 (1.5); 5.8839 (0.8); 5.8740 (0.8);5.8703 (1.6); 5.8577 (1.1); 5.8446 (1.6); 5.8311 (0.8); 5.3280 (1.0);5.3109 (3.2); 5.2938 (3.3); 5.2768 (1.0); 5.2406 (1.0); 5.2363 (2.3);5.2330 (2.4); 5.2287 (1.0); 5.1977 (0.9); 5.1933 (2.0); 5.1900 (2.1);5.1858 (0.9); 5.1558 (1.1); 5.1522 (2.7); 5.1487 (2.6); 5.1451 (1.0);5.1300 (1.0); 5.1264 (2.5); 5.1230 (2.4); 5.1193 (1.0); 3.9914 (0.8);3.9872 (1.5); 3.9813 (1.7); 3.9772 (2.0); 3.9727 (2.6); 3.9674 (2.8);3.9633 (2.0); 3.9592 (1.6); 3.9533 (1.5); 3.9490 (0.8); 1.7140 (16.0);1.6970 (15.9); 1.5575 (6.2); 0.0080 (3.4); −0.0002 (99.9); −0.0085 (3.4)III-046: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.5182 (0.7); 7.3013 (0.6);7.2961 (0.8); 7.2877 (0.8); 7.2814 (3.6); 7.2798 (3.4); 7.2759 (2.3);7.2733 (2.1); 7.2684 (3.4); 7.2593 (131.7); 7.2519 (4.6); 7.2475 (2.7);7.2464 (2.7); 7.2415 (0.7); 7.2355 (1.1); 7.1457 (2.2); 7.1415 (2.7);7.1359 (0.8); 7.1291 (1.2); 7.1246 (2.2); 7.1213 (1.8); 7.0879 (2.2);7.0824 (0.7); 7.0709 (0.8); 7.0662 (3.3); 7.0612 (0.8); 7.0497 (0.6);7.0443 (1.7); 6.9953 (0.7); 5.2764 (1.6); 5.2594 (1.6); 3.3302 (0.6);3.3124 (1.2); 3.3002 (1.3); 3.2974 (1.2); 3.2857 (1.2); 3.2802 (0.6);3.2680 (0.6); 1.6990 (7.7); 1.6820 (7.6); 1.6004 (1.2); 1.5823 (2.5);1.5641 (2.8); 1.5389 (16.0); 0.9486 (4.0); 0.9302 (8.2); 0.9116 (3.5);0.0080 (1.7); −0.0002 (49.5); −0.0084 (1.7) III-047: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3029 (0.7); 7.2988 (1.0); 7.2975 (1.0); 7.2932 (0.9);7.2873 (3.0); 7.2813 (4.2); 7.2774 (2.2); 7.2744 (4.1); 7.2650 (6.0);7.2594 (82.3); 7.2528 (5.6); 7.2491 (2.2); 7.2448 (0.7); 7.2427 (0.7);7.2368 (1.4); 7.2354 (1.3); 7.1528 (3.0); 7.1487 (3.7); 7.1431 (1.0);7.1363 (1.6); 7.1318 (2.9); 7.1285 (2.4); 7.0901 (3.0); 7.0846 (0.9);7.0759 (0.6); 7.0731 (1.1); 7.0686 (4.4); 7.0633 (1.1); 7.0519 (0.8);7.0465 (2.3); 6.7700 (0.6); 5.2980 (0.6); 5.2809 (2.1); 5.2639 (2.1);5.2469 (0.6); 3.2195 (1.6); 3.2173 (1.6); 3.2027 (2.8); 3.1875 (1.6);1.7060 (10.3); 1.6890 (10.1); 1.5458 (16.0); 1.0121 (0.6); 1.0098 (0.5);0.9921 (1.0); 0.9799 (0.5); 0.9744 (0.6); 0.9721 (0.6); 0.5169 (0.8);0.5116 (2.0); 0.5087 (2.6); 0.5060 (1.5); 0.4961 (1.0); 0.4915 (2.3);0.4886 (2.1); 0.4837 (0.8); 0.2395 (0.9); 0.2331 (1.2); 0.2307 (1.3);0.2275 (1.8); 0.2238 (2.0); 0.2184 (1.7); 0.2121 (1.2); 0.2060 (0.8);0.0079 (1.1); −0.0002 (31.3); −0.0085 (1.0) III-048: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.2782 (1.2); 7.2741 (0.8); 7.2715 (0.8); 7.2595 (48.7);7.2465 (0.7); 7.2441 (0.8); 7.1435 (0.7); 7.1393 (0.8); 7.1224 (0.7);7.1192 (0.6); 7.0878 (0.7); 7.0661 (1.0); 7.0443 (0.5); 1.7046 (2.3);1.6876 (2.2); 1.5377 (16.0); 0.9226 (3.6); 0.9059 (3.5); 0.0079 (0.7);−0.0002 (19.6); −0.0085 (0.8) III-049: ¹H-NMR(400.0 MHz, CDCl3): δ =7.5182 (0.7); 7.3099 (1.3); 7.3044 (1.9); 7.3000 (1.2); 7.2882 (5.9);7.2819 (6.1); 7.2763 (3.0); 7.2733 (4.0); 7.2690 (10.6); 7.2593 (120.4);7.2527 (4.8); 7.2465 (5.8); 7.2337 (0.6); 7.2288 (0.6); 7.2250 (0.7);7.1562 (4.7); 7.1520 (5.9); 7.1464 (1.7); 7.1398 (2.4); 7.1352 (4.5);7.1318 (3.8); 7.0970 (0.6); 7.0899 (4.5); 7.0844 (1.5); 7.0677 (7.5);7.0632 (1.8); 7.0517 (1.3); 7.0463 (3.7); 6.9952 (0.7); 6.7242 (1.0);5.9218 (0.6); 5.9082 (1.3); 5.8948 (1.1); 5.8824 (1.5); 5.8788 (0.9);5.8687 (0.8); 5.8652 (1.6); 5.8519 (1.2); 5.8395 (1.6); 5.8259 (0.8);5.3246 (1.1); 5.3076 (3.5); 5.2906 (3.5); 5.2736 (1.1); 5.2346 (1.0);5.2303 (2.5); 5.2270 (2.4); 5.2227 (1.1); 5.1917 (0.9); 5.1874 (2.2);5.1840 (2.1); 5.1832 (2.0); 5.1798 (1.0); 5.1490 (2.7); 5.1456 (2.6);5.1420 (1.1); 5.1232 (2.5); 5.1198 (2.4); 5.1163 (1.0); 3.9846 (1.9);3.9801 (2.1); 3.9753 (2.2); 3.9703 (3.5); 3.9659 (3.5); 3.9615 (2.2);3.9562 (2.0); 3.9519 (1.9); 3.9477 (0.8); 1.7111 (16.0); 1.6941 (15.8);1.5438 (11.2); 0.0080 (1.6); −0.0002 (45.9); −0.0085 (1.8) III-050:¹H-NMR(400.0 MHz, CDCl3): δ = 7.5182 (0.7); 7.3083 (1.7); 7.3027 (1.6);7.2982 (1.1); 7.2940 (1.0); 7.2863 (5.1); 7.2804 (5.4); 7.2751 (2.6);7.2715 (3.5); 7.2676 (10.4); 7.2594 (124.2); 7.2545 (6.3); 7.2510 (3.3);7.2452 (4.7); 7.2421 (2.4); 7.2227 (0.7); 7.1547 (4.2); 7.1506 (5.4);7.1449 (1.5); 7.1382 (2.3); 7.1336 (4.2); 7.1303 (3.5); 7.0968 (0.6);7.0897 (4.3); 7.0842 (1.4); 7.0755 (0.8); 7.0727 (1.5); 7.0682 (6.4);7.0630 (1.6); 7.0515 (1.2); 7.0461 (3.4); 6.9954 (0.7); 6.6541 (0.8);5.2893 (0.9); 5.2723 (3.1); 5.2553 (3.1); 5.2383 (0.9); 3.3270 (1.2);3.3174 (1.2); 3.3093 (2.3); 3.3026 (1.5); 3.2997 (2.3); 3.2942 (2.2);3.2849 (2.4); 3.2765 (1.1); 3.2673 (1.2); 1.6956 (15.0); 1.6786 (14.9);1.6152 (0.6); 1.5968 (2.5); 1.5787 (5.1); 1.5604 (6.1); 1.5466 (5.9);1.5426 (6.2); 1.5243 (0.9); 0.9427 (7.9); 0.9243 (16.0); 0.9057 (6.9);0.0080 (1.6); −0.0002 (45.1); −0.0085 (1.5) III-051: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.2870 (1.5); 7.2817 (1.0); 7.2733 (1.8); 7.2695 (2.4);7.2678 (2.2); 7.2594 (66.9); 7.2437 (0.7); 7.1620 (1.0); 7.1580 (1.3);7.1455 (0.6); 7.1410 (1.0); 7.1377 (0.8); 7.0922 (1.0); 7.0706 (1.6);7.0486 (0.8); 5.2774 (0.7); 5.2604 (0.8); 3.2163 (0.8); 3.2020 (1.0);3.1990 (1.0); 3.1847 (0.9); 1.7023 (3.6); 1.6853 (3.6); 1.5378 (16.0);0.5081 (0.7); 0.5053 (0.9); 0.5027 (0.6); 0.4881 (0.8); 0.4852 (0.7);0.2234 (0.7); 0.2196 (0.7); 0.2141 (0.6); 0.0080 (0.9); −0.0002 (25.2);−0.0084 (1.0) III-052: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3059 (0.9);7.3017 (1.2); 7.3004 (1.3); 7.2960 (0.9); 7.2918 (0.8); 7.2842 (4.3);7.2784 (4.4); 7.2730 (2.2); 7.2694 (3.1); 7.2655 (9.4); 7.2637 (7.7);7.2595 (64.8); 7.2529 (3.9); 7.2488 (2.2); 7.2465 (1.7); 7.2431 (4.1);7.2410 (2.3); 7.2213 (0.6); 7.1523 (3.7); 7.1481 (4.5); 7.1425 (1.3);7.1358 (2.0); 7.1312 (3.7); 7.1279 (3.0); 7.0892 (3.8); 7.0837 (1.2);7.0749 (0.8); 7.0722 (1.3); 7.0677 (5.5); 7.0625 (1.4); 7.0510 (1.1);7.0456 (2.9); 6.6798 (0.7); 5.2943 (0.8); 5.2773 (2.6); 5.2603 (2.6);5.2433 (0.8); 3.2352 (0.6); 3.2189 (1.0); 3.2022 (1.8); 3.1857 (2.2);3.1694 (1.2); 3.1499 (1.4); 3.1351 (1.8); 3.1330 (1.7); 3.1180 (1.7);3.1019 (0.8); 3.0998 (0.8); 3.0850 (0.7); 1.8452 (0.7); 1.8283 (1.4);1.8115 (1.8); 1.7947 (1.5); 1.7780 (0.8); 1.7011 (12.6); 1.6840 (12.6);1.5563 (2.4); 0.9167 (16.0); 0.9149 (15.6); 0.9000 (15.5); 0.8982(15.0); 0.0079 (0.8); −0.0002 (23.7); −0.0085 (0.9) III-058:¹H-NMR(400.0 MHz, CDCl3): δ = 7.3094 (0.6); 7.3045 (0.7); 7.2874 (3.7);7.2817 (1.9); 7.2735 (2.9); 7.2690 (4.1); 7.2595 (62.6); 7.2542 (3.4);7.2517 (3.4); 7.2478 (1.1); 7.2445 (0.7); 7.2413 (1.2); 7.1648 (2.2);7.1608 (2.9); 7.1552 (1.1); 7.1482 (1.5); 7.1437 (2.5); 7.1405 (2.1);7.0883 (2.1); 7.0828 (0.7); 7.0712 (0.8); 7.0667 (3.2); 7.0616 (0.8);7.0501 (0.8); 7.0447 (1.7); 5.3521 (1.5); 5.3351 (1.5); 5.2981 (1.5);4.1430 (1.7); 4.1293 (2.0); 4.1190 (1.9); 4.1057 (1.8); 3.7752 (2.5);3.7680 (16.0); 1.7188 (7.2); 1.7017 (7.3); 1.6799 (0.8); 1.5424 (9.5);0.0080 (0.7); −0.0002 (23.2); −0.0085 (0.9) III-059: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.2989 (1.0); 7.2938 (1.0); 7.2909 (1.6); 7.2807 (3.2);7.2776 (4.2); 7.2673 (3.8); 7.2600 (66.7); 7.2516 (3.5); 7.2476 (3.4);7.2450 (3.0); 7.2348 (1.4); 7.2313 (1.6); 7.2158 (0.6); 7.1569 (1.7);7.1529 (2.1); 7.1456 (1.9); 7.1414 (2.7); 7.1358 (2.1); 7.1326 (1.4);7.1289 (1.1); 7.1244 (1.9); 7.1212 (1.5); 7.0870 (2.7); 7.0825 (1.1);7.0656 (4.6); 7.0444 (2.3); 7.0361 (0.6); 7.0253 (0.7); 5.2978 (3.2);5.2467 (1.2); 5.2298 (1.4); 5.2142 (1.6); 5.1973 (1.4); 4.3949 (0.7);4.3779 (0.8); 3.6839 (1.7); 3.6745 (1.5); 3.6659 (16.0); 3.6614 (13.9);2.8912 (0.7); 2.8847 (0.7); 2.8696 (0.8); 2.2657 (0.6); 2.2543 (0.5);2.2486 (0.8); 2.2317 (0.7); 2.2260 (0.5); 2.0075 (0.5); 1.9977 (1.2);1.9860 (0.9); 1.9815 (1.6); 1.9656 (1.3); 1.9558 (0.8); 1.9448 (1.1);1.9309 (0.7); 1.9146 (0.6); 1.8564 (0.8); 1.8371 (0.7); 1.8301 (0.5);1.8236 (0.6); 1.7699 (0.6); 1.7530 (0.5); 1.7360 (0.7); 1.7204 (0.7);1.7051 (0.6); 1.6867 (6.4); 1.6791 (5.4); 1.6696 (6.3); 1.6621 (5.4);1.6484 (0.8); 1.6414 (0.6); 1.5600 (14.0); 0.0080 (0.8); −0.0002 (23.2);−0.0085 (0.8) III-063: ¹H-NMR(400.0 MHz, CDCl3): δ = 7.3021 (0.5);7.2857 (2.3); 7.2795 (1.3); 7.2719 (2.2); 7.2675 (2.9); 7.2660 (2.8);7.2593 (23.0); 7.2501 (1.7); 7.2453 (0.9); 7.2434 (0.9); 7.1572 (1.4);7.1528 (1.5); 7.1472 (0.6); 7.1409 (0.9); 7.1363 (1.4); 7.1329 (1.2);7.0883 (1.2); 7.0712 (0.5); 7.0665 (1.9); 7.0448 (1.0); 5.2854 (0.6);5.2819 (0.6); 5.2424 (0.6); 5.2388 (0.5); 5.1413 (0.7); 5.1378 (0.7);5.1155 (0.7); 5.1120 (0.6); 3.9979 (0.5); 3.9938 (0.8); 3.9897 (0.6);3.9835 (0.8); 3.9798 (1.3); 3.9761 (0.8); 3.9700 (0.6); 3.9658 (0.8);1.7663 (16.0); 1.5476 (6.4); −0.0002 (8.0) III-066: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.4567 (0.6); 7.4530 (0.7); 7.4443 (0.7); 7.4390 (1.2);7.4345 (1.3); 7.4220 (1.2); 7.4205 (1.2); 7.4182 (1.2); 7.4132 (1.0);7.4044 (0.9); 7.3998 (1.8); 7.3953 (1.2); 7.3798 (2.2); 7.3764 (1.9);7.3616 (1.7); 7.3573 (1.3); 7.2609 (29.4); 7.2601 (28.7); 7.2400 (2.5);7.2386 (2.5); 7.2199 (1.2); 7.2064 (1.1); 7.2011 (1.1); 7.1879 (1.1);7.1815 (1.6); 7.1751 (1.3); 7.1710 (1.2); 7.1621 (1.1); 7.1568 (1.2);7.1501 (1.9); 7.1296 (1.6); 7.1255 (1.8); 7.1051 (2.7); 7.0837 (1.7);7.0805 (2.6); 7.0593 (1.4); 7.0563 (1.3); 7.0460 (1.0); 7.0419 (1.4);7.0366 (1.5); 7.0315 (1.4); 7.0265 (1.1); 7.0206 (1.1); 7.0154 (1.2);7.0104 (1.1); 6.9968 (0.9); 6.9810 (0.8); 5.9546 (0.5); 5.9409 (1.0);5.9278 (0.9); 5.9151 (1.2); 5.9120 (0.8); 5.9010 (0.8); 5.8980 (1.3);5.8848 (1.0); 5.8722 (1.3); 5.8583 (0.6); 5.2979 (4.2); 5.2554 (1.9);5.2515 (1.9); 5.2483 (0.9); 5.2124 (2.3); 5.2089 (2.1); 5.1866 (2.1);5.1832 (2.0); 4.9068 (16.0); 4.7635 (0.8); 4.0409 (2.5); 4.0373 (1.7);4.0267 (4.6); 4.0161 (1.7); 4.0125 (2.4); 1.5684 (7.0); 1.2557 (0.5);−0.0002 (10.8); −0.0009 (10.1); −0.0083 (0.5) III-068: ¹H-NMR(400.0 MHz,CDCl3): δ = 7.3990 (0.8); 7.3930 (0.8); 7.3776 (1.4); 7.3616 (1.0);7.3561 (1.0); 7.3405 (0.7); 7.3108 (0.8); 7.2595 (56.5); 7.2116 (0.6);7.1876 (0.9); 7.1825 (0.9); 7.1695 (1.3); 7.1627 (1.2); 7.1558 (1.0);7.1495 (1.4); 7.1373 (0.9); 7.1251 (1.2); 7.1043 (0.8); 7.0424 (0.9);7.0365 (1.0); 7.0314 (0.9); 7.0152 (0.8); 6.9953 (0.9); 6.9866 (1.8);6.9677 (2.6); 6.9466 (1.6); 6.6319 (0.5); 5.9223 (0.5); 5.8968 (0.6);5.8798 (0.7); 5.8670 (0.6); 5.8539 (0.6); 5.2631 (1.2); 5.2202 (1.1);5.1851 (1.2); 5.1821 (1.3); 5.1565 (1.2); 4.8347 (8.3); 4.0253 (1.5);4.0110 (2.6); 3.9969 (1.5); 1.5380 (16.0); −0.0002 (21.3) III-069:¹H-NMR(400.0 MHz, CDCl3): δ = 7.4723 (0.6); 7.4569 (1.2); 7.4507 (1.1);7.4414 (0.7); 7.4354 (2.3); 7.4293 (0.8); 7.4199 (1.1); 7.4138 (1.3);7.3984 (0.6); 7.2612 (32.0); 7.2350 (1.0); 7.2298 (1.0); 7.2168 (1.0);7.2105 (1.6); 7.2043 (1.2); 7.1937 (1.2); 7.1914 (1.2); 7.1860 (1.1);7.1727 (1.7); 7.1695 (1.1); 7.1531 (1.6); 7.1482 (1.7); 7.1287 (1.4);7.0892 (0.8); 7.0852 (1.1); 7.0796 (1.2); 7.0751 (1.2); 7.0701 (0.9);7.0637 (0.8); 7.0584 (0.8); 7.0536 (0.8); 7.0101 (3.0); 6.9918 (4.4);6.9885 (4.4); 6.9703 (3.0); 5.9519 (0.6); 5.9381 (1.3); 5.9259 (0.8);5.9123 (1.5); 5.9090 (0.8); 5.8985 (0.8); 5.8952 (1.6); 5.8817 (1.0);5.8694 (1.6); 5.8556 (0.7); 5.3019 (1.0); 5.2979 (3.3); 5.2949 (2.3);5.2907 (1.0); 5.2590 (0.8); 5.2549 (1.9); 5.2519 (1.9); 5.2477 (0.9);5.2151 (1.1); 5.2117 (2.5); 5.2085 (2.3); 5.2051 (1.0); 5.1894 (1.0);5.1859 (2.3); 5.1827 (2.2); 5.1793 (0.9); 4.8934 (16.0); 4.0443 (1.4);4.0405 (2.3); 4.0367 (1.6); 4.0300 (2.7); 4.0263 (4.3); 4.0226 (2.6);4.0160 (1.6); 4.0121 (2.3); 4.0083 (1.3); 1.5740 (7.8); −0.0002 (11.3)

B. Formulation Examples

a) A dusting product is obtained by mixing 10 parts by weight of acompound of the formula (I) and/or salts thereof and 90 parts by weightof talc as inert substance and comminuting the mixture in an impactmill.

b) A readily water-dispersible, wettable powder is obtained by mixing 25parts by weight of a compound of the formula (I) and/or salts thereof,64 parts by weight of kaolin-containing quartz as inert substance, 10parts by weight of potassium lignosulfonate and 1 part by weight ofsodium oleoylmethyltaurate as wetting agent and dispersant and grindingin a pinned-disc mill.

c) A readily water-dispersible dispersion concentrate is obtained bymixing 20 parts by weight of a compound of the formula (I) and/or saltsthereof with 6 parts by weight of alkylphenol polyglycol ether (®TritonX 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and71 parts by weight of paraffinic mineral oil (boiling range e.g. about255 to more than 277° C.) and grinding to a fineness of below 5 micronsin an attrition ball mill.

d) An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the formula (I) and/or salts thereof, 75 parts by weight ofcyclohexanone as solvent and 10 parts by weight of oxethylatednonylphenol as emulsifier.

e) Water-dispersible granules are obtained by mixing

75 parts by weight of a compound of the formula (I) and/or saltsthereof,

10 parts by weight of calcium lignosulfonate,

5 parts by weight of sodium lauryl sulfate,

3 parts by weight of polyvinyl alcohol and

7 parts by weight of kaolin,

grinding the mixture in a pinned-disc mill, and granulating the powderin a fluidized bed by spray application of water as a granulatingliquid.

f) Water-dispersible granules are also obtained by homogenizing andprecomminuting, in a colloid mill,

25 parts by weight of a compound of the formula (I) and/or saltsthereof,

5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,

2 parts by weight of sodium oleoylmethyltaurate,

1 part by weight of polyvinyl alcohol,

17 parts by weight of calcium carbonate and

50 parts by weight of water,

then grinding the mixture in a bead mill and atomizing and drying theresulting suspension in a spray tower by means of a one-phase nozzle.

C. Biological Examples

1. Pre-Emergence Herbicidal Action and Crop Plant Compatibility

Seeds of mono- and dicotyledonous weed plants are placed in plastic potsin sandy loam soil (doubly sown with one species each of mono- ordicotyledonous weed plants per pot) and covered with soil. The compoundsof the invention, formulated in the form of wettable powders (WP) or asemulsion concentrates (EC), are then applied onto the surface of thecovering soil as aqueous suspension or emulsion with addition of 0.5%additive at a water application rate equivalent to 600 litres perhectare. After the treatment, the pots are placed in a greenhouse andkept under good growth conditions for the trial plants. After about 3weeks, the effect of the preparations is scored visually in comparisonwith untreated controls as percentages. For example, 100% activity=theplants have died, 0% activity=like control plants.

In Tables 4.1-4.15 and 5.1-5.16 below, the following abbreviations areused:

ALOMY: Alopecurus myosuroides AMARE: Amaranthus retroflexus AVEFA: Avenafatua CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli HORMU:Hordeum murinum LOLRI: Lolium rigidum MATIN: Matricaria inodora PHBPU:Pharbitis purpurea POLCO: Polygonum convolvulus SETVI: Setaria viridisSTEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor

Tables 4.1-4.15 below show the effects of selected compounds of thegeneral formula (I) according to Tables 1 to 3 on various harmful plantsat an application rate corresponding to 1280 or 320 g/ha, which havebeen obtained by the aforementioned experimental method.

TABLE 4.1 Pre-emergence action at 1280 g/ha against ALOMY in % Ex.Dosage No. [g/ha] ALOMY I-002 1280 80 I-007 1280 80 I-008 1280 100 I-0561280 90 I-057 1280 90 I-061 1280 90 I-067 1280 90 I-070 1280 90 I-0721280 80

TABLE 4.2 Pre-emergence action at 1280 g/ha against CYPES in % Ex.Dosage No. [g/ha] CYPES I-003 1280 100 I-006 1280 100 I-012 1280 100I-021 1280 100 I-022 1280 100 I-056 1280 90 I-061 1280 90 I-067 1280 90I-070 1280 80

TABLE 4.3 Pre-emergence action at 1280 g/ha against ECHCG in % Ex.Dosage No. [g/ha] ECHCG I-011 1280 80 I-022 1280 80 I-054 1280 90 I-0551280 100 I-057 1280 80 I-061 1280 90 I-067 1280 80 I-069 1280 80 I-0701280 90 I-076 1280 90 I-079 1280 90 I-081 1280 90 I-085 1280 100 I-0931280 100 I-097 1280 100 I-098 1280 100 I-100 1280 100 I-101 1280 100I-102 1280 100 I-107 1280 100 I-111 1280 100 I-114 1280 90 I-120 1280 90I-121 1280 100 I-122 1280 100 I-125 1280 100 I-130 1280 100 I-131 1280100 I-133 1280 90 I-134 1280 100 I-136 1280 100 I-137 1280 100 I-1381280 100 I-139 1280 100 I-140 1280 90 I-141 1280 100 I-142 1280 100I-145 1280 100 I-164 1280 100 I-167 1280 100 I-168 1280 90 I-169 1280100 I-171 1280 90 II-04 1280 100 III-001 1280 90 III-003 1280 100III-004 1280 100 III-005 1280 100 III-006 1280 100 III-015 1280 100III-016 1280 100 III-022 1280 100 III-023 1280 90 III-024 1280 90III-027 1280 100 III-033 1280 90 III-053 1280 100 III-058 1280 90III-067 1280 100 III-068 1280 100 III-069 1280 100

TABLE 4.4 Pre-emergence action at 1280 g/ha against SETVI in % Ex.Dosage No. [g/ha] SETVI I-008 1280 90 I-015 1280 90 I-022 1280 100 I-0251280 80 I-036 1280 80 I-054 1280 90 I-055 1280 100 I-056 1280 100 I-0571280 90 I-061 1280 100 I-063 1280 100 I-067 1280 100 I-069 1280 90 I-0701280 90 I-072 1280 80 I-076 1280 100 I-078 1280 100 I-079 1280 100 I-0811280 100 I-085 1280 100 I-086 1280 90 I-088 1280 90 I-091 1280 90 I-0921280 100 I-093 1280 100 I-094 1280 100 I-095 1280 100 I-097 1280 100I-098 1280 90 I-100 1280 100 I-101 1280 100 I-102 1280 100 I-107 1280 90I-108 1280 100 I-111 1280 90 I-114 1280 100 I-118 1280 90 I-119 1280 100I-120 1280 100 I-121 1280 100 I-123 1280 90 I-124 1280 100 I-125 1280100 I-126 1280 100 I-127 1280 100 I-129 1280 100 I-130 1280 100 I-1311280 100 I-132 1280 100 I-133 1280 100 I-134 1280 100 I-136 1280 100I-137 1280 100 I-138 1280 100 I-139 1280 100 I-140 1280 100 I-141 1280100 I-142 1280 100 I-143 1280 100 I-144 1280 100 I-145 1280 100 I-1561280 90 I-164 1280 100 I-165 1280 100 I-166 1280 90 I-167 1280 100 I-1691280 100 I-170 1280 100 I-171 1280 100 III-001 1280 100 III-003 1280 100III-004 1280 100 III-005 1280 100 III-006 1280 100 III-015 1280 100III-016 1280 100 III-017 1280 100 III-018 1280 90 III-019 1280 100III-022 1280 100 III-023 1280 100 III-024 1280 100 III-026 1280 90III-027 1280 90 III-033 1280 100 III-053 1280 100 III-054 1280 90III-056 1280 90 III-058 1280 90 III-066 1280 90 III-067 1280 100 III-0681280 100 III-069 1280 100

TABLE 4.5 Pre-emergence action at 1280 g/ha against AMARE in % Ex.Dosage No. [g/ha] AMARE I-002 1280 100 I-003 1280 100 I-004 1280 90I-006 1280 100 I-007 1280 100 I-008 1280 100 I-011 1280 90 I-012 1280100 I-015 1280 90 I-016 1280 100 I-021 1280 100 I-022 1280 100 I-0231280 90 I-025 1280 90 I-026 1280 80 I-036 1280 80 I-046 1280 90 I-0511280 90 I-054 1280 100 I-055 1280 100 I-056 1280 100 I-057 1280 100I-061 1280 100 I-063 1280 80 I-066 1280 100 I-067 1280 100 I-069 1280 90I-070 1280 100 I-072 1280 90 I-076 1280 100 I-078 1280 90 I-079 1280 100I-081 1280 100 I-085 1280 100 I-086 1280 100 I-088 1280 90 I-091 1280100 I-092 1280 100 I-093 1280 100 I-094 1280 100 I-095 1280 100 I-0971280 100 I-098 1280 100 I-099 1280 90 I-100 1280 100 I-101 1280 90 I-1021280 100 I-107 1280 90 I-108 1280 90 I-112 1280 100 I-114 1280 100 I-1181280 100 I-119 1280 100 I-120 1280 100 I-121 1280 90 I-122 1280 100I-123 1280 100 I-125 1280 100 I-126 1280 100 I-127 1280 100 I-128 1280100 I-129 1280 100 I-130 1280 100 I-131 1280 100 I-132 1280 100 I-1331280 100 I-134 1280 100 I-136 1280 100 I-137 1280 100 I-138 1280 100I-139 1280 100 I-140 1280 90 I-141 1280 100 I-142 1280 100 I-143 1280100 I-144 1280 100 I-145 1280 90 I-155 1280 90 I-156 1280 100 I-164 1280100 I-165 1280 100 I-166 1280 90 I-167 1280 100 I-168 1280 100 I-1691280 100 I-170 1280 100 I-171 1280 100 II-04 1280 100 II-06 1280 90II-07 1280 90 II-09 1280 90 II-13 1280 100 II-14 1280 100 III-003 1280100 III-004 1280 100 III-005 1280 90 III-006 1280 90 III-015 1280 100III-016 1280 100 III-017 1280 100 III-018 1280 90 III-019 1280 90III-022 1280 90 III-023 1280 90 III-024 1280 100 III-026 1280 90 III-0271280 100 III-029 1280 90 III-033 1280 90 III-053 1280 90 III-054 1280 90III-056 1280 100 III-058 1280 100 III-066 1280 90 III-067 1280 100III-068 1280 90 III-069 1280 90

TABLE 4.6 Pre-emergence action at 320 g/ha against AMARE in % Ex. No.Dosage [g/ha] AMARE I-002 320 100 I-003 320 100 I-006 320 80 I-007 32080 I-008 320 100 I-012 320 100 I-014 320 100 I-015 320 90 I-021 320 100I-022 320 100 I-023 320 90 I-025 320 90 I-046 320 90 I-047 320 90 I-054320 100 I-054 320 100 I-055 320 100 I-056 320 80 I-057 320 100 I-057 32090 I-061 320 90 I-064 320 100 I-067 320 90 I-069 320 90 I-070 320 100I-072 320 80 I-079 320 80 I-081 320 80 I-082 320 90 I-100 320 100 I-101320 90 I-102 320 90 I-125 320 100 I-130 320 100 I-137 320 90 I-139 320100 I-141 320 90 I-165 320 90 III-003 320 100 III-004 320 80 III-006 32090 HI-069 320 100

TABLE 4.7 Pre-emergence action at 1280 g/ha against MATIN in % Ex. No.Dosage [g/ha] MATIN I-002 1280 100 I-003 1280 100 I-008 1280 90 I-0121280 100 I-015 1280 90 I-016 1280 90 I-021 1280 90 I-022 1280 90 I-0231280 100 I-026 1280 90 I-046 1280 90 I-048 1280 80 I-056 1280 90 I-0571280 100 I-061 1280 90 I-067 1280 90 I-069 1280 90 I-070 1280 90 I-0721280 80

TABLE 4.8 Pre-emergence action at 1280 g/ha against AVEFA in % Ex. No.Dosage [g/ha] AVEFA I-056 1280 80 I-057 1280 80 I-067 1280 80

TABLE 4.9 Pre-emergence action at 1280 g/ha against PHBPU in % Ex. No.Dosage [g/ha] PHBPU I-003 1280 80 I-015 1280 100 I-057 1280 90 I-0611280 90 I-069 1280 80 I-070 1280 90 I-072 1280 90

TABLE 4.10 Pre-emergence action at 320 g/ha against POLCO in % Ex. No.Dosage [g/ha] POLCO I-001 320 90 I-008 320 80 I-054 320 100 I-055 320 90I-056 320 80 I-057 320 90 I-064 320 100 I-070 320 80 I-072 320 90 I-075320 80 I-079 320 80 I-081 320 100 I-082 320 80 I-101 320 100 I-102 320100 I-125 320 100 I-130 320 90 I-137 320 100 I-139 320 90 III-003 320100 III-006 320 90 III-015 320 90 III-069 320 90 320 90

TABLE 4.11 Pre-emergence action at 1280 g/ha against STEME in % Ex. No.Dosage [g/ha] STEME I-002 1280 100 I-003 1280 100 I-006 1280 100 I-0071280 90 I-008 1280 100 I-015 1280 90 I-016 1280 80 I-020 1280 80 I-0211280 90 I-022 1280 90 I-054 1280 100 I-055 1280 100 I-056 1280 100 I-0571280 100 I-061 1280 100 I-063 1280 80 I-067 1280 90 I-069 1280 90 I-0701280 90 I-072 1280 90 I-076 1280 100 I-079 1280 100 I-081 1280 100 I-0861280 90 I-088 1280 100 I-092 1280 100 I-093 1280 100 I-094 1280 100I-095 1280 100 I-097 1280 100 I-098 1280 100 I-100 1280 100 I-101 1280100 I-102 1280 90 I-107 1280 100 I-109 1280 100 I-111 1280 100 I-1121280 100 I-114 1280 100 I-119 1280 100 I-120 1280 100 I-121 1280 100I-123 1280 100 I-124 1280 100 I-125 1280 100 I-126 1280 100 I-127 1280100 I-128 1280 90 I-129 1280 100 I-130 1280 100 I-132 1280 100 I-1331280 100 I-134 1280 100 I-135 1280 100 I-136 1280 100 I-137 1280 100I-138 1280 100 I-139 1280 100 I-140 1280 100 I-141 1280 90 I-142 1280100 I-143 1280 90 I-145 1280 100 I-150 1280 100 I-155 1280 100 I-1561280 100 I-164 1280 100 I-165 1280 100 I-166 1280 90 I-167 1280 100I-168 1280 100 I-169 1280 100 I-170 1280 100 I-171 1280 100 II-04 1280100 II-06 1280 90 II-07 1280 90 II-09 1280 100 II-13 1280 90 III-0011280 100 III-003 1280 100 III-004 1280 100 III-005 1280 100 III-006 1280100 III-008 1280 100 III-015 1280 100 III-016 1280 100 III-017 1280 100III-018 1280 100 III-019 1280 100 III-022 1280 100 III-023 1280 100III-024 1280 100 III-025 1280 100 III-027 1280 100 III-033 1280 100III-053 1280 100 III-056 1280 100 III-058 1280 100 III-066 1280 90III-067 1280 90 III-068 1280 90 III-069 1280 90

TABLE 4.12 Pre-emergence action at 320 g/ha against STEME in % Ex. No.Dosage [g/ha] STEME I-002 320 80 I-054 320 100 I-055 320 100 I-057 32080 I-061 320 90 I-064 320 90 I-070 320 80 I-075 320 80 I-081 320 80I-100 320 90 I-102 320 90 I-125 320 90 I-130 320 90 I-137 320 90 I-139320 100 I-141 320 80 III-003 320 100 III-069 320 100

TABLE 4.13 Pre-emergence action at 1280 g/ha against VIOTR in % Ex. No.Dosage [g/ha] VIOTR I-021 1280 90 I-022 1280 90 I-046 1280 90 I-051 128090 I-056 1280 80 I-057 1280 100 I-061 1280 90 I-063 1280 100 I-066 128090 I-067 1280 100 I-069 1280 100 I-070 1280 90 I-072 1280 80

TABLE 4.14 Pre-emergence action at 320 g/ha against VERPE in % Ex. No.Dosage [g/ha] VERPE I-002 320 100 I-003 320 100 I-008 320 90 I-014 320100 I-015 320 90 I-021 320 90 I-022 320 100 I-023 320 90 I-025 320 80I-047 320 90 I-054 320 100 I-055 320 90 I-057 320 90 I-081 320 80 I-082320 80 I-100 320 100 I-102 320 80 I-125 320 90 I-130 320 100 I-137 32090 I-139 320 100 I-165 320 100 III-003 320 100 III-004 320 100 III-006320 90 III-015 320 90 III-069 320 100

TABLE 4.15 Pre-emergence action at 320 g/ha against HORMU in % Ex. No.Dosage [g/ha] HORMU I-056 320 80 I-064 320 90 I-125 320 90 I-130 320 100I-139 320 90 III-069 320 90

As the results show, inventive compounds, for example compound nos.I-002, I-003, I-008, I-021, I-022, I-056, I-057, I-061, I-067, I-069,I-070, I-072, I-121, I-125, I-138, I-139, II-013, III-003, III-022,III-027, III-053, III-069 and other compounds from tables 4.1-4.15, showgood herbicidal efficacy against harmful plants in the case ofpre-emergence treatment. For example, compounds no. I-008, I-056, I-057,I-061, I-067, I-070 and I-072 applied by the pre-emergence method havevery good action (80% to 100% herbicidal action) against harmful plantssuch as Alopecurus myosuroides, Amaranthus retroflexus, Matricariainodora, Polygonum convolvulus, Setaria viridis and Stellaria media atan application rate of 1.28 kg of active substance or less per hectare.

2. Post-Emergence Herbicidal Action and Crop Plant Compatibility

Seeds of mono- and dicotyledonous weed plants are placed in plastic potsin sandy loam soil (twin sowing with one species each of mono- ordicotyledonous weed plants per pot), covered with soil and cultivated ina greenhouse under controlled growth conditions. 2 to 3 weeks aftersowing, the test plants are treated at the one-leaf stage. The compoundsof the invention, formulated in the form of wettable powders (WP) or asemulsion concentrates (EC), are applied to the green parts of the plantsas aqueous suspension or emulsion with addition of 0.5% additive at awater application rate equivalent to 600 litres per hectare. After thetest plants have been kept in the greenhouse under optimum growthconditions for about 3 weeks, the activity of the preparations is ratedvisually in comparison to untreated controls. For example, 100%activity=the plants have died, 0% activity=like control plants.

Tables 5.1-5.16 below show the effects of selected compounds of thegeneral formula (I) according to Tables 1 to 3 on various harmful plantsat an application rate corresponding to 1280 or 320 g/ha, which havebeen obtained by the aforementioned experimental method.

TABLE 5.1 Post-emergence action at 1280 g/ha against ALOMY in % Ex. No.Dosage [g/ha] ALOMY I-002 1280 80 I-006 1280 80 I-021 1280 80 I-022 128080 I-046 1280 80 I-051 1280 80 I-056 1280 90 I-057 1280 90 I-061 1280 90I-067 1280 100 I-070 1280 80 I-072 1280 80

TABLE 5.2 Post-emergence action at 1280 g/ha against AVEFA in % Ex. No.Dosage [g/ha] AVEFA I-009 1280 80 I-012 1280 80 I-022 1280 80 I-025 128080 I-036 1280 80 I-051 1280 80 I-056 1280 90 I-057 1280 90

TABLE 5.3 Post-emergence action at 1280 g/ha against ECHCG in % Ex. No.Dosage [g/ha] ECHCG I-002 1280 80 I-003 1280 80 I-016 1280 80 I-021 128080 I-022 1280 80 I-054 1280 90 I-055 1280 100 I-061 1280 80 I-067 128090 I-070 1280 80 I-072 1280 80 I-079 1280 100 I-081 1280 90 I-093 1280100 I-097 1280 100 I-098 1280 100 I-100 1280 90 I-107 1280 90 I-120 128090 I-123 1280 90 I-125 1280 90 I-126 1280 90 I-130 1280 100 I-136 1280100 I-137 1280 100 I-141 1280 100 I-143 1280 100 I-164 1280 90 I-1671280 90 I-169 1280 90 I-171 1280 100 III-003 1280 100 III-019 1280 90III-022 1280 90 III-027 1280 90 III-053 1280 100

TABLE 5.4 Post-emergence action at 1280 g/ha against LOLRI in % Ex. No.Dosage [g/ha] LOLRI I-057 1280 80 I-067 1280 90 I-130 1280 90 I-171 1280100

TABLE 5.5 Post-emergence action at 1280 g/ha against SETVI in % Ex. No.Dosage [g/ha] SETVI I-002 1280 80 I-006 1280 90 I-009 1280 80 I-016 128080 I-022 1280 80 I-054 1280 100 I-056 1280 80 I-061 1280 80 I-063 128080 I-072 1280 80 I-079 1280 100 I-081 1280 90 I-089 1280 100 I-097 128090 I-098 1280 90 I-125 1280 90 I-126 1280 90 I-137 1280 90 I-145 1280 90I-164 1280 100 I-165 1280 90 I-169 1280 90 I-171 1280 100 III-001 1280100 III-003 1280 100 III-019 1280 90 III-022 1280 100 III-023 1280 100III-026 1280 100 III-027 1280 100 III-033 1280 100 III-053 1280 100III-054 1280 100 III-058 1280 100 III-066 1280 100 III-067 1280 100III-068 1280 90

TABLE 5.6 Post-emergence action at 1280 g/ha against AMARE in % Ex.Dosage No. [g/ha] AMARE I-002 1280 90 I-003 1280 80 I-004 1280 80 I-0051280 80 I-006 1280 100 I-007 1280 80 I-008 1280 80 I-009 1280 80 I-0121280 80 I-015 1280 80 I-016 1280 80 I-021 1280 80 I-022 1280 80 I-0231280 80 I-025 1280 80 I-026 1280 80 I-027 1280 80 I-038 1280 90 I-0461280 80 I-054 1280 100 I-055 1280 90 I-056 1280 80 I-057 1280 80 I-0611280 80 I-069 1280 90 I-070 1280 80 I-072 1280 80 I-076 1280 100 I-0781280 100 I-079 1280 100 I-081 1280 100 I-085 1280 100 I-086 1280 100I-088 1280 100 I-089 1280 100 I-091 1280 100 I-092 1280 100 I-093 1280100 I-094 1280 100 I-095 1280 100 I-098 1280 100 I-099 1280 90 I-1001280 90 I-101 1280 100 I-102 1280 90 I-107 1280 100 I-109 1280 100 I-1111280 100 I-114 1280 100 I-119 1280 100 I-123 1280 90 I-125 1280 90 I-1261280 100 I-127 1280 90 I-128 1280 90 I-129 1280 100 I-130 1280 90 I-1331280 90 I-134 1280 90 I-136 1280 90 I-137 1280 90 I-141 1280 90 I-1431280 100 I-156 1280 100 I-164 1280 100 I-165 1280 100 I-166 1280 100I-169 1280 100 I-170 1280 90 I-171 1280 90 III-001 1280 100 III-003 1280100 III-004 1280 100 III-006 1280 100 III-016 1280 90 III-017 1280 100III-018 1280 100 III-019 1280 100 III-022 1280 90 III-025 1280 90III-026 1280 90 III-027 1280 90 III-033 1280 90 III-058 1280 90

TABLE 5.7 Post-emergence action at 320 g/ha against AMARE in % Ex.Dosage No. [g/ha] AMARE I-002 320 80 I-005 320 80 I-008 320 80 I-012 32080 I-014 320 80 I-015 320 80 I-021 320 80 I-022 320 80 I-025 320 80I-047 320 80 I-054 320 90 I-055 320 90 I-056 320 80 I-057 320 80 I-061320 80 I-079 320 80 I-081 320 90 I-082 320 80 I-100 320 80 I-101 320 80I-102 320 80 I-125 320 90 I-130 320 90 I-137 320 80 I-139 320 90 I-141320 90 III-003 320 80 III-004 320 80 III-006 320 80 III-015 320 80III-069 320 90

TABLE 5.8 Post-emergence action at 1280 g/ha against MATIN in % Ex.Dosage No. [g/ha] MATIN I-002 1280 80 I-003 1280 80 I-006 1280 80 I-0081280 90 I-011 1280 90 I-015 1280 90 I-021 1280 80 I-022 1280 80 I-0231280 80 I-025 1280 80 I-036 1280 80 I-038 1280 80 I-046 1280 80 I-0511280 90 I-054 1280 100 I-055 1280 100 I-056 1280 80 I-057 1280 90 I-0631280 80 I-066 1280 80 I-067 1280 80 I-070 1280 80 I-072 1280 80 I-0761280 90 I-079 1280 100 I-081 1280 100 I-085 1280 90 I-088 1280 90 I-0931280 100 I-095 1280 100 I-097 1280 100 I-098 1280 90 I-100 1280 90 I-1011280 90 I-102 1280 100 I-107 1280 100 I-111 1280 90 I-114 1280 90 I-1191280 90 I-120 1280 90 I-121 1280 90 I-123 1280 90 I-124 1280 90 I-1251280 90 I-127 1280 90 I-129 1280 100 I-130 1280 90 I-131 1280 90 I-1321280 90 I-133 1280 90 I-136 1280 90 I-137 1280 90 I-139 1280 90 I-1411280 90 I-142 1280 90 I-143 1280 100 I-145 1280 90 I-156 1280 90 I-1641280 100 I-165 1280 100 I-166 1280 100 I-168 1280 90 I-169 1280 90 I-1711280 90 II-13 1280 100 III-019 1280 90 III-026 1280 90 III-027 1280 100III-053 1280 90 III-056 1280 90 III-058 1280 100 III-067 1280 90 III-0681280 90

TABLE 5.9 Post-emergence action at 320 g/ha against MATIN in % Ex.Dosage No. [g/ha] MATIN I-003 320 80 I-008 320 90 I-011 320 90 I-015 32090 I-022 320 80 I-036 320 80 I-047 320 80 I-051 320 90 I-054 320 90I-056 320 80 I-057 320 80 I-064 320 80 I-066 320 80 I-075 320 80 I-079320 80 I-081 320 80 I-082 320 80 I-100 320 80 I-101 320 90 I-102 320 80I-125 320 80 I-130 320 90 I-137 320 80 I-139 320 80 I-141 320 80 III-069320 80

TABLE 5.10 Post-emergence action at 320 g/ha against PHBPU in % Ex.Dosage No. [g/ha] PHBPU I-002 320 80 I-003 320 80 I-004 320 80 I-005 32080 I-006 320 80 I-012 320 80 I-014 320 80 I-015 320 80 I-016 320 80I-021 320 80 I-023 320 80 I-026 320 90 I-029 320 80 I-036 320 80 I-038320 80 I-046 320 80 I-047 320 80 I-051 320 80 I-054 320 100 I-055 320 80I-056 320 80 I-057 320 90 I-061 320 80 I-064 320 80 I-066 320 90 I-069320 80 I-070 320 90 I-075 320 90 I-079 320 90 I-081 320 90 I-082 320 90I-100 320 90 I-101 320 90 I-102 320 90 I-125 320 80 I-137 320 90 I-165320 80 III-003 320 80 III-004 320 80 III-006 320 80 III-015 320 80

TABLE 5.11 Post-emergence action at 320 g/ha against POLCO in % Ex.Dosage No. [g/ha] POLCO I-004 320 80 I-008 320 80 I-011 320 80 I-014 32080 I-022 320 80 I-051 320 80 I-054 320 80 I-055 320 80 I-056 320 80I-057 320 80 I-061 320 80 I-064 320 80 I-075 320 80 I-079 320 80 I-081320 80 I-100 320 90 I-125 320 80 I-130 320 90 I-137 320 90 I-139 320 90I-165 320 80 III-004 320 80 III-015 320 80 III-069 320 80

TABLE 5.12 Post-emergence action at 1280 g/ha against STEME in % Ex.Dosage No. [g/ha] STEME I-002 1280 90 I-003 1280 80 I-006 1280 80 I-0081280 90 I-011 1280 80 I-012 1280 80 I-016 1280 80 I-021 1280 80 I-0221280 80 I-023 1280 80 I-036 1280 80 I-046 1280 80 I-051 1280 80 I-0541280 100 I-055 1280 100 I-056 1280 90 I-057 1280 90 I-061 1280 80 I-0671280 90 I-069 1280 80 I-070 1280 90 I-072 1280 80 I-079 1280 100 I-0811280 100 I-085 1280 100 I-088 1280 100 I-093 1280 100 I-097 1280 100I-098 1280 90 I-100 1280 90 I-102 1280 100 I-107 1280 90 I-109 1280 90I-111 1280 90 I-119 1280 90 I-121 1280 100 I-125 1280 90 I-126 1280 100I-130 1280 100 I-131 1280 90 I-132 1280 100 I-133 1280 100 I-134 1280100 I-136 1280 100 I-137 1280 100 I-138 1280 100 I-139 1280 90 I-1401280 100 I-141 1280 90 I-142 1280 100 I-143 1280 100 I-145 1280 100I-150 1280 100 I-164 1280 100 I-165 1280 100 I-167 1280 100 I-168 1280100 I-169 1280 100 I-170 1280 100 I-171 1280 100 II-04 1280 100 II-061280 100 II-08 1280 90 II-09 1280 100 III-008 1280 100 III-022 1280 100III-025 1280 100 III-027 1280 90 III-053 1280 100 III-058 1280 100III-067 1280 100

TABLE 5.13 Post-emergence action at 320 g/ha against STEME in % Ex.Dosage No. [g/ha] STEME I-002 320 80 I-003 320 80 I-008 320 90 I-012 32080 I-014 320 80 I-021 320 80 I-022 320 80 I-023 320 80 I-036 320 80I-046 320 80 I-047 320 80 I-054 320 90 I-055 320 80 I-057 320 80 I-064320 90 I-067 320 80 I-081 320 80 I-100 320 80 I-130 320 90 I-137 320 90I-139 320 80 I-141 320 90 III-069 320 90

TABLE 5.14 Post-emergence action at 320 g/ha against VIOTR in % Ex.Dosage No. [g/ha] VIOTR I-005 320 80 I-012 320 80 I-023 320 80 I-025 32080 I-026 320 80 I-036 320 80 I-046 320 80 I-047 320 90 I-051 320 90I-054 320 90 I-055 320 100 I-061 320 80 I-063 320 90 I-064 320 100 I-066320 80 I-067 320 80 I-075 320 100 I-079 320 100 I-081 320 100 I-082 320100 I-100 320 100 I-101 320 100 I-102 320 90 I-125 320 90 I-130 320 90I-137 320 80 I-139 320 80 I-141 320 90 I-165 320 80 III-006 320 80III-015 320 80

TABLE 5.15 Post-emergence action at 320 g/ha against VERPE in % Ex.Dosage No. [g/ha] VERPE I-002 320 80 I-007 320 90 I-008 320 90 I-011 32080 I-015 320 90 I-022 320 80 I-025 320 80 I-029 320 80 I-036 320 80I-038 320 80 I-046 320 80 I-047 320 80 I-048 320 80 I-051 320 80 I-054320 80 I-055 320 80 I-056 320 90 I-057 320 80 I-075 320 80 I-079 320 80I-081 320 80 I-082 320 80 I-100 320 90 I-101 320 80 I-102 320 80 I-125320 80 I-130 320 90 I-137 320 90 I-165 320 80 III-003 320 80 III-006 32080 III-015 320 90 III-069 320 90

TABLE 5.16 Post-emergence action at 320 g/ha against HORMU in % Ex.Dosage No. [g/ha] HORMU I-055 320 80 I-057 320 80 I-064 320 90 I-067 32080 I-075 320 80 I-125 320 90 I-130 320 80 I-137 320 80 I-139 320 80I-141 320 80 III-069 320 80

As the results from Tables 5.1-5.16 show, compounds of the inventionhave good herbicidal post-emergence efficacy against a broad spectrum ofweed grasses and weeds.

As the results show, compounds of the invention, for example compoundNos. I-002, I-003, I-006, I-014, 1-021, 1-054, 1-072, 11-04, 111-058 andother compounds from Tables 5.1-5.16, when applied post-emergence, havevery good herbicidal efficacy against harmful plants. For example,compounds Nos. I-002, I-006, I-022, I-056 and I-072 applied by thepost-emergence method have very good herbicidal action (80% to 100%herbicidal action) against harmful plants such as Alopecurusmyosuroides, Amaranthus retroflexus, Matricaria inodora, Setariaviridis, Pharbitis purpurea and Stellaria media at an application rateof 1.28 kg of active substance or less per hectare.

1. A compound comprising a 1,5-Diphenylpyrazolyl-3-oxyalkyl acid and/ora 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acid of formula (I), and/or anagrochemically acceptable salt thereof,

where A is selected from the group consisting of A1-A3,

R¹ is selected from the group consisting of OR^(1a) and NR⁹R¹⁰; whereR^(1a) is selected from the group consisting of hydrogen; methyl, ethylwhich is unsubstituted or substituted by one or more substituentsselected from the group consisting of halogen, (C₃-C₆)-cycloalkyl,(C₁-C₄)-trialkylsilyl, (C₁-C₆)-alkoxy, cyano and nitro; (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl; (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl which isunsubstituted or substituted by one or more substituents selected fromthe group consisting of halogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl;(C₁-C₄)-alkyl-SO—(C₁-C₄)-alkyl, (C₁-C₄)-alkyl-SO₂—(C₁-C₄)-alkyl;heterocyclyl, heteroaryl and aryl which is unsubstituted or substitutedby one or more substituents selected from the group consisting ofhalogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl; heterocyclyl-(C₁-C₄)-alkyl,heteroaryl-(C₁-C₄)-alkyl and aryl-(C₁-C₄)-alkyl, where the heterocyclyl,heteroaryl and aryl is unsubstituted or substituted by one or moresubstituents selected from the group consisting of halogen,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl; R⁹ is selected from the groupconsisting of hydrogen, (C₁-C₁₂)-alkyl; R¹⁰ is selected from the groupconsisting of hydrogen; aryl, heteroaryl, heterocyclyl, which isunsubstituted or substituted by one or more substituents selected fromthe group consisting of halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl;(C₃-C₇)-cycloalkyl-(C₁-C₄)-alkyl, heterocyclyl-(C₁-C₄)-alkyl,heteroaryl-(C₁-C₄)-alkyl, aryl-(C₁-C₄)-alkyl, aryl-(C₁-C₄)-alkoxy; wherethe cycloalkyl, heterocyclyl, heteroaryl and aryl is unsubstituted orsubstituted by one or more substituents selected from the groupconsisting of halogen, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl; (C₁-C₁₂)-alkyl;(C₃-C₈)-cycloalkyl, (C₂-C₁₂)-alkenyl, (C₅-C₈)-cycloalkenyl,(C₂-C₁₂)-alkynyl; where the abovementioned alkyl, cycloalkenyl, alkenyl,cycloalkenyl and alkynyl radicals are unsubstituted or eachindependently substituted by m radicals selected from the groupconsisting of cyano, nitro, OR⁵, S(O)_(n)R⁵, SO₂NR⁶R⁷, C(O)OR⁸, CONR⁶R⁸,COR⁶, NR⁶R⁸, NR⁶COR⁸, NR⁶CONR⁸R⁸, NR⁶CO₂R⁸, NR⁶SO₂R⁸, NR⁶SO₂NR⁶R⁸,C(R⁶)═NOR⁸; (C₁-C₁₂)-haloalkyl; S(O)_(n)R⁵, cyano, nitro, OR⁵, SO₂NR⁶R⁷,C₀₂R⁸, COR⁸, NR⁶R⁸, NR⁶COR⁸, NR⁶CO₂R⁸, NR⁶SO₂R⁸;  or R⁹ and R¹⁰ togetherwith the nitrogen atom to which they are attached form a saturated,partially or fully unsaturated five-, six- or seven-membered ring whichis optionally mono- to hexasubstituted by radicals from the groupconsisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, OR⁵,S(O)_(n)R⁵, CO₂R⁸, CONR⁶R⁸, COR⁶ and C(R⁶)═NOR⁸ and which, in additionto this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfuratoms and q elements from the group consisting of NR⁷, CO and NCOR⁷ asring atoms; R⁵ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkylor aryl; R⁶ is hydrogen or R⁵; R⁷ is hydrogen, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, (C₃-C₄)-alkenyl or (C₃-C₄)-alkynyl; R⁸ is hydrogen,(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₃-C₄)-alkenyl or (C₃-C₄)-alkynyl;R^(2a) is selected from the group consisting of hydrogen; methyl; R^(2b)is hydrogen; R³ is selected from the group consisting of halogen, cyano,isocyano, NO₂; (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₄)-alkyloxycarbonyl; (C₂-C₃)-alkenyl, (C₂-C₃)-haloalkenyl;(C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl; (C₁-C₂)-alkyl-S(O)_(n) and(C₁-C₂)-haloalkyl-S(O)_(n); CHO; NH₂; R⁴ is phenyl, where the phenylradical is unsubstituted or mono- or polysubstituted by a radicalselected from the group consisting of halogen, cyano, isocyano, nitro;(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₃)-haloalkoxy; (C₂-C₃)-alkenyl,(C₂-C₃)-haloalkenyl, (C₁-C₆)-alkoxy; (C₂-C₃)-alkynyl,(C₂-C₃)-haloalkynyl, (C₁-C₄)-alkyl-S(O)_(n); CHO,(C₁-C₄)-alkyloxycarbonyl and NH₂; R¹² is selected from the groupconsisting of halogen, cyano, isocyano, NO₂; (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₄)-alkyloxycarbonyl, (C₁-C₆)-alkoxy, (C₁-C₃)-haloalkoxy,(C₁-C₄)-alkyl-S(O)_(n); (C₂-C₃)-alkenyl, (C₂-C₃)-haloalkenyl;(C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl; NH₂; and where the indices are asfollows: m is 0, 1 or 2; n is 0, 1 or 2; o is 0, 1 or 2; p is 0 or 1; qis 0 or 1; r is 3, 4, 5 or 6; and s is 0, 1, 2, 3, 4 or 5, excluding thefollowing compounds: [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]aceticacid, {[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}aceticacid, {[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}aceticacid, ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.
 2. The compoundof the formula (I) according to claim 1 and/or an agrochemicallyacceptable salt thereof, where A is selected from the group consistingof A1-A3,

R¹ is selected from the group consisting of OR^(1a) and NR⁹R¹⁰; whereR^(1a) is selected from the group consisting of hydrogen; methyl, ethylwhich is unsubstituted or substituted by one or more substituentsselected from the group consisting of halogen, (C₃-C₆)-cycloalkyl,(C₁-C₄)-trialkylsilyl, (C₁-C₄)-alkoxy, cyano and nitro; (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl; aryl-(C₁-C₄)-alkyl, where the aryl is unsubstitutedor substituted by one or more substituents selected from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl; R⁹ is selectedfrom the group consisting of hydrogen, (C₁-C₆)-alkyl; R¹⁰ is selectedfrom the group consisting of hydrogen; (C₃-C₇)-cycloalkyl-(C₁-C₄)-alkyl,aryl-(C₁-C₄)-alkyl, aryl-(C₁-C₄)-alkoxy, where the cycloalkyl and arylis unsubstituted or substituted by one or more substituents selectedfrom the group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl;(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl; (C₃-C₈)-cycloalkyl; where the abovementioned alkyl, alkenyl, alkynyl and cycloalkenylradicals are unsubstituted or are each independently substituted by mradicals selected from the group consisting of Cyano, C(O)OR⁸;(C₁-C₆)-haloalkyl R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl;R^(2a) is selected from the group consisting of hydrogen; methyl; R^(2b)is hydrogen; R³ is selected from the group consisting of fluorine,chlorine, bromine, iodine, cyano, isocyano, NO₂; (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkyloxycarbonyl;(C₂-C₃)-alkynyl, (C₂-C₃)-haloalkynyl; R⁴ is phenyl, where the phenylradical is unsubstituted or mono- or polysubstituted by a radicalselected from the group consisting of fluorine, chlorine, bromine;methyl, ethyl; methoxy, ethoxy; R¹² is selected from the groupconsisting of halogen, cyano, nitro; (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₃)-haloalkoxy; (C₁-C₆)-alkoxy; and where the indices are asfollows: m is 0, 1 or 2; s is 0, 1, 2, 3, excluding the compounds:[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.
 3. The compoundof the formula (I) according to claim 1 and/or an agrochemicallyacceptable salt thereof, where A is A1;

R¹ is selected from the group consisting of OR^(1a) and NR⁹R¹⁰; whereR^(1a) is selected from the group consisting of hydrogen; methyl, ethyl,trimethylsilylmethyl; 1-propenyl, 2-propenyl; benzyl, 1-phenylethyl,2-phenylethyl, where the phenyl radical in each of the three groupsmentioned is unsubstituted or substituted by halogen; R⁹ is hydrogen;R¹⁰ is selected from the group consisting of hydrogen;cyclopropylmethyl; benzyl, 1-phenylethyl, 2-phenylethyl, benzyloxy,where the phenyl radical in each of the four groups mentioned isunsubstituted or substituted by halogen; methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, where the abovementioned radicals areunsubstituted or are each independently monosubstituted by a C(O)OR⁸radical; cyclopropyl, cyclobutyl, cyclopentyl, where the three radicalsmentioned are unsubstituted or are each independently monosubstituted bya C(O)OR⁸ radical; 1-propenyl, 2-propenyl, 2-methyl-2-propenyl,prop-2-yn-1-yl, but-2-yn-1-yl; R⁸ is hydrogen, methyl, ethyl; R^(2a) isselected from the group consisting of hydrogen; methyl; R^(2b) ishydrogen; R³ is selected from the group consisting of fluorine,chlorine, bromine, iodine, cyano, NO₂; trifluoromethyl; ethynyl;C(O)Omethyl; R⁴ is phenyl, where the phenyl radical is unsubstituted ormono- or polysubstituted by a radical selected from the group consistingof fluorine, chlorine, bromine; methyl, ethyl; methoxy, ethoxy; R¹² isselected from the group consisting of fluorine, chlorine, NO₂;trifluoromethyl, methoxy, ethoxy; and where the indices are as follows:s 1, 2, 3, excluding the compounds:[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.
 4. The compoundof formula (I) according claim 1 and/or an agrochemically acceptablesalt thereof, where A is A1

R¹ is selected from the group consisting of OR^(1a) and NR⁹R¹⁰; whereR^(1a) is selected from the group consisting of hydrogen; methyl, ethyl;2-propenyl; R⁹ is hydrogen; R¹⁰ is selected from the group consisting ofcyclopentyl monosubstituted by C(O)OR⁸; cyclopropylmethyl; CH₂C(O)OR⁸,CH₂CH₂C(O)OR⁸; 2-propenyl, prop-2-yn-1-yl; R⁸ is hydrogen, methyl,ethyl; R^(2a) is selected from the group consisting of hydrogen; methyl;R^(2b) is hydrogen; R³ is selected from the group consisting ofchlorine, bromine, iodine, cyano, NO₂; R⁴ is phenyl, where the phenylradical is unsubstituted or mono- or polysubstituted by a radicalselected from the group consisting of fluorine, chlorine; R¹² isselected from the group consisting of fluorine, chlorine; and where theindices are as follows: s is 1, 2, excluding the compounds:[(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetic acid,{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetic acid,ethyl [(4-chloro-1,5-diphenyl-1H-pyrazol-3-yl)oxy]acetate, ethyl{[4-chloro-5-(4-methylphenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,ethyl{[4-chloro-5-(3-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl]oxy}acetate,2-(4-chloro-1,5-diphenyl-pyrazol-3-yl)oxypropanoic acid,2-(4-bromo-1,5-diphenylpyrazol-3-yl)oxypropanoic acid.
 5. A process forpreparing one or more compounds of formula (Ia) and/or an agrochemicallyacceptable salt thereof according to claim 1 comprising reacting one ormore compounds of formulae (II) and (III) to give one or more compoundsof formula (IV), which are reacted with one or more compounds of formula(V) to give one or more compounds of formula (Ia),

in which R⁴, R^(2a), R^(2b), R^(1a), R³, and A have the definition givenabove, and X is chlorine, bromine or iodine.
 6. A process for preparingone or more compounds of formula (Ib) and/or an agrochemicallyacceptable salt thereof according to claim 1 comprising reacting one ormore compounds of formula (Ia) in which R⁴, R^(2a), R^(2b), R^(1a), R³,and A have the definitions given above further with one or morecompounds of formula (VI) to give one or more compounds of formula (Ib).


7. An agrochemical composition comprising a) at least one compound offormula (I) or an agrochemically acceptable salt thereof as defined inclaim 1, and b) one or more auxiliaries and/or additives customary incrop protection.
 8. The agrochemical composition comprising a) at leastone compound of the formula (I) or an agrochemically acceptable saltthereof as defined in claim 1, b) one or more active agrochemicalingredients other than component a), and optionally c) one or moreauxiliaries and/or additives customary in crop protection.
 9. A methodof controlling unwanted one or more plants or for regulating the growthof one or more plants, comprising applying an effective amount of atleast one compound of the formula (I) and/or an agrochemicallyacceptable salt thereof, as defined in claim 1, to the plants, seedand/or an area in which the plants grow.
 10. A product comprising one ormore compounds of the formula (I) and/or an agrochemically acceptablesalt thereof, as defined in claim 1, wherein said product is anherbicide and/or a plant growth regulator.
 11. The product according toclaim 10, wherein the compound of formula (I) or an agrochemicallyacceptable salt thereof is used for controlling harmful one or moreplants and/or for regulating growth in one or more plant crops.
 12. Theproduct according to claim 11, wherein the crop plants are transgenic ornontransgenic crop plants.